The Experts below are selected from a list of 771 Experts worldwide ranked by ideXlab platform
Jean-pierre Hurvois - One of the best experts on this subject based on the ideXlab platform.
-
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.
-
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.
-
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
Van Ha Vu - One of the best experts on this subject based on the ideXlab platform.
-
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.
-
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.
Oleksandr O. Grygorenko - One of the best experts on this subject based on the ideXlab platform.
-
5 6 7 8 tetrahydropyrido 4 3 c pyridazine a lead oriented scaffold with two diversity points
ChemInform, 2014Co-Authors: A V Borisov, Volodymyr V. Voloshchuk, Maxim A. Nechayev, Oleksandr O. GrygorenkoAbstract:The five step sequence for the synthesis of the title compounds includes the reaction of 4-piperidone derivative (I) with glyoxylic acid and hydrazine as the key step.
-
5,6,7,8-Tetrahydropyrido[4,3-c]pyridazine: A Lead-Oriented Scaffold with Two Diversity Points
Synthesis, 2013Co-Authors: Alexander V. Borisov, Volodymyr V. Voloshchuk, Maxim A. Nechayev, Oleksandr O. GrygorenkoAbstract:An approach to the derivatives of 5,6,7,8-tetrahydropyrido[4,3- c ]pyridazine, a lead-oriented scaffold with two diversity points, was developed. The method included five steps starting from the readily available 4-piperidone derivatives and allowed for the preparation of the target compounds in 32–35% overall yields. The key step of the sequence included one-pot solvent-free reaction of the corresponding 4-piperidone derivative, glyoxylic acid, and hydrazine.
Fadila Louafi - One of the best experts on this subject based on the ideXlab platform.
-
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.
-
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.
-
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.
-
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.
-
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.
-
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