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Jean-pierre Hurvois - One of the best experts on this subject based on the ideXlab platform.
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electrochemical access to 8 1 phenyl ethyl 1 4 dioxa 8 aza spiro 4 5 decane 7 carbonitrile application to the asymmetric syntheses of myrtine and alkaloid 241d
Journal of Organic Chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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Electrochemical access to 8-(1-phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-7-carbonitrile. Application to the asymmetric syntheses of (+)-myrtine and alkaloid (+)-241D.
The Journal of organic chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (-)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation-reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1-3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er's were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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electrochemical access to 8 1 phenyl ethyl 1 4 dioxa 8 aza spiro 4 5 decane 7 carbonitrile application to the asymmetric syntheses of myrtine and alkaloid 241d
Journal of Organic Chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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Electrochemical Access to 8‑(1-Phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-7-carbonitrile. Application to the Asymmetric Syntheses of (+)-Myrtine and Alkaloid (+)-241D
2014Co-Authors: Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents
Fadila Louafi - One of the best experts on this subject based on the ideXlab platform.
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electrochemical access to 8 1 phenyl ethyl 1 4 dioxa 8 aza spiro 4 5 decane 7 carbonitrile application to the asymmetric syntheses of myrtine and alkaloid 241d
Journal of Organic Chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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Electrochemical access to 8-(1-phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-7-carbonitrile. Application to the asymmetric syntheses of (+)-myrtine and alkaloid (+)-241D.
The Journal of organic chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (-)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation-reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1-3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er's were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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electrochemical access to 8 1 phenyl ethyl 1 4 dioxa 8 aza spiro 4 5 decane 7 carbonitrile application to the asymmetric syntheses of myrtine and alkaloid 241d
Journal of Organic Chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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Electrochemical Access to 8‑(1-Phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-7-carbonitrile. Application to the Asymmetric Syntheses of (+)-Myrtine and Alkaloid (+)-241D
2014Co-Authors: Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents
Vincent Dorcet - One of the best experts on this subject based on the ideXlab platform.
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electrochemical access to 8 1 phenyl ethyl 1 4 dioxa 8 aza spiro 4 5 decane 7 carbonitrile application to the asymmetric syntheses of myrtine and alkaloid 241d
Journal of Organic Chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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Electrochemical access to 8-(1-phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-7-carbonitrile. Application to the asymmetric syntheses of (+)-myrtine and alkaloid (+)-241D.
The Journal of organic chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (-)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation-reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1-3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er's were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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electrochemical access to 8 1 phenyl ethyl 1 4 dioxa 8 aza spiro 4 5 decane 7 carbonitrile application to the asymmetric syntheses of myrtine and alkaloid 241d
Journal of Organic Chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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Electrochemical Access to 8‑(1-Phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-7-carbonitrile. Application to the Asymmetric Syntheses of (+)-Myrtine and Alkaloid (+)-241D
2014Co-Authors: Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents
Nicolas Girard - One of the best experts on this subject based on the ideXlab platform.
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electrochemical access to 8 1 phenyl ethyl 1 4 dioxa 8 aza spiro 4 5 decane 7 carbonitrile application to the asymmetric syntheses of myrtine and alkaloid 241d
Journal of Organic Chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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Electrochemical access to 8-(1-phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-7-carbonitrile. Application to the asymmetric syntheses of (+)-myrtine and alkaloid (+)-241D.
The Journal of organic chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (-)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation-reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1-3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er's were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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electrochemical access to 8 1 phenyl ethyl 1 4 dioxa 8 aza spiro 4 5 decane 7 carbonitrile application to the asymmetric syntheses of myrtine and alkaloid 241d
Journal of Organic Chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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Electrochemical Access to 8‑(1-Phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-7-carbonitrile. Application to the Asymmetric Syntheses of (+)-Myrtine and Alkaloid (+)-241D
2014Co-Authors: Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents
Ronan Marion - One of the best experts on this subject based on the ideXlab platform.
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electrochemical access to 8 1 phenyl ethyl 1 4 dioxa 8 aza spiro 4 5 decane 7 carbonitrile application to the asymmetric syntheses of myrtine and alkaloid 241d
Journal of Organic Chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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Electrochemical access to 8-(1-phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-7-carbonitrile. Application to the asymmetric syntheses of (+)-myrtine and alkaloid (+)-241D.
The Journal of organic chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (-)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation-reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1-3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er's were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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electrochemical access to 8 1 phenyl ethyl 1 4 dioxa 8 aza spiro 4 5 decane 7 carbonitrile application to the asymmetric syntheses of myrtine and alkaloid 241d
Journal of Organic Chemistry, 2014Co-Authors: Van Ha Vu, Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
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Electrochemical Access to 8‑(1-Phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-7-carbonitrile. Application to the Asymmetric Syntheses of (+)-Myrtine and Alkaloid (+)-241D
2014Co-Authors: Fadila Louafi, Ronan Marion, Nicolas Girard, Vincent Dorcet, Thierry Roisnel, Jean-pierre HurvoisAbstract:The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted Piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (−)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation–reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1–3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er’s were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents
