The Experts below are selected from a list of 222 Experts worldwide ranked by ideXlab platform
Matthew L Clarke - One of the best experts on this subject based on the ideXlab platform.
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diastereoselective and branched aldehyde selective tandem hydroformylation hemiaminal formation synthesis of functionalized piperidines and amino alcohols
Organic Letters, 2017Co-Authors: Rachael Pittaway, Jose Fuentes, Matthew L ClarkeAbstract:Starting from readily available Allylglycine, a tandem hydroformylation–hemiaminal formation reaction has been developed for the synthesis of chiral functionalized piperidines, with very good diastereoselectivity and branched regioselectivity using Rh/(S,S,S)-BOBPHOS catalysts. Tandem hydroformylation–hemiacetal formation also proceeds with good diastereoselectivity (88:12), with the hemiacetal product being hydrogenated with retention of stereochemistry to give a chiral intermediate used in the synthesis of the new antibiotic nemonoxacin.
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Diastereoselective and Branched-Aldehyde-Selective Tandem Hydroformylation–Hemiaminal Formation: Synthesis of Functionalized Piperidines and Amino Alcohols
2017Co-Authors: Rachael Pittaway, José A. Fuentes, Matthew L ClarkeAbstract:Starting from readily available Allylglycine, a tandem hydroformylation–hemiaminal formation reaction has been developed for the synthesis of chiral functionalized piperidines, with very good diastereoselectivity and branched regioselectivity using Rh/(S,S,S)-BOBPHOS catalysts. Tandem hydroformylation–hemiacetal formation also proceeds with good diastereoselectivity (88:12), with the hemiacetal product being hydrogenated with retention of stereochemistry to give a chiral intermediate used in the synthesis of the new antibiotic nemonoxacin
Rachael Pittaway - One of the best experts on this subject based on the ideXlab platform.
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diastereoselective and branched aldehyde selective tandem hydroformylation hemiaminal formation synthesis of functionalized piperidines and amino alcohols
Organic Letters, 2017Co-Authors: Rachael Pittaway, Jose Fuentes, Matthew L ClarkeAbstract:Starting from readily available Allylglycine, a tandem hydroformylation–hemiaminal formation reaction has been developed for the synthesis of chiral functionalized piperidines, with very good diastereoselectivity and branched regioselectivity using Rh/(S,S,S)-BOBPHOS catalysts. Tandem hydroformylation–hemiacetal formation also proceeds with good diastereoselectivity (88:12), with the hemiacetal product being hydrogenated with retention of stereochemistry to give a chiral intermediate used in the synthesis of the new antibiotic nemonoxacin.
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Diastereoselective and Branched-Aldehyde-Selective Tandem Hydroformylation–Hemiaminal Formation: Synthesis of Functionalized Piperidines and Amino Alcohols
2017Co-Authors: Rachael Pittaway, José A. Fuentes, Matthew L ClarkeAbstract:Starting from readily available Allylglycine, a tandem hydroformylation–hemiaminal formation reaction has been developed for the synthesis of chiral functionalized piperidines, with very good diastereoselectivity and branched regioselectivity using Rh/(S,S,S)-BOBPHOS catalysts. Tandem hydroformylation–hemiacetal formation also proceeds with good diastereoselectivity (88:12), with the hemiacetal product being hydrogenated with retention of stereochemistry to give a chiral intermediate used in the synthesis of the new antibiotic nemonoxacin
Floris L. Van Delft - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of a protected enantiomerically pure 2-deoxystreptamine derivative from D-Allylglycine
Tetrahedron Letters, 2004Co-Authors: Guuske Frederike Busscher, Floris P. J. T. Rutjes, Floris L. Van DelftAbstract:A diastereoselective synthetic route from D-Allylglycine to the enantiopure (protected) 2-deoxystreptamine derivative 14 is presented. Key steps involve two consecutive chain extensions-with crucial stereodirective roles for the amino protective groups, ring closure by olefin metathesis, face selective dihydroxylation, cyclic sulfate formation and finally opening with azide. The resulting 2-deoxystreptamine derivative is ideally protected for the preparation of 4,5- or 4,6-linked aminoglycoside antibiotics. (C) 2004 Elsevier Ltd. All rights reserved.
André Luxen - One of the best experts on this subject based on the ideXlab platform.
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development of solid supported methodology for the preparation of peptidoglycan fragments containing 2s 6r diaminopimelic acid
Tetrahedron Letters, 2016Co-Authors: Justine Simon, Nicolas Lamborelle, Christian Lemaire, Bernard Joris, Astrid Zervosen, André LuxenAbstract:Abstract Herein, we describe the development of an efficient solid-supported methodology for the stereoselective synthesis of two peptides containing (2 S ,6 R )-diaminopimelic acid, ( S )-Ala-γ-( R )-Glu-(2 S ,6 R )-A 2 pm-( R )-Ala 1 and γ-( R )-Glu-(2 S ,6 R )-A 2 pm 2 . The platform consists of a Wang resin anchored by an amino acid chain including Allylglycine. By olefin cross metathesis with vinylglycine, unsaturated protected (2 S ,6 R )-A 2 pm was fixed on solid support. Peptides were achieved by cleavage of cross metathesis products from resin, followed by reduction of double bonds along removing of protecting groups. Furthermore, this efficient solid phase approach will lead to peptide and muropeptide libraries.
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stereoselective synthesis of stable isotopomers of meso 2 6 diaminopimelic acid
2014Co-Authors: Nicolas Lamborelle, Justine Simon, Christian Lemaire, Bernard Joris, André LuxenAbstract:References [1] M. J. Pucci et al., Clin. Microbiol. Rev. 2013, 26, 792-821. [2] M. S. Butler et al., J. Antibiot. 2013, 66, 571-591. [3] A. Zervosen et al., Molecules 2012, 17, 12478-17505. Figure 4 | 13C-Allylglycine synthesis. i) Cbz-Cl, NaOH (aq), toluene, 0 °C rt ; tBuOH, DCC, DMAP, CH2Cl2 ; H2 (6 bar), Pd/C (10%wt, dry), HCl, MeOH ; Ph2C=NH, CH2Cl2, MgSO4. ii) CH2=CH-CH2-Br, KOH (50%wt, aq), toluene, CH2Cl2, -20 °C. iii) citric acid (10%wt, aq), THF ; Fmoc-OSu, THF, H2O (51%, 7 steps).
Guuske Frederike Busscher - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of a protected enantiomerically pure 2-deoxystreptamine derivative from D-Allylglycine
Tetrahedron Letters, 2004Co-Authors: Guuske Frederike Busscher, Floris P. J. T. Rutjes, Floris L. Van DelftAbstract:A diastereoselective synthetic route from D-Allylglycine to the enantiopure (protected) 2-deoxystreptamine derivative 14 is presented. Key steps involve two consecutive chain extensions-with crucial stereodirective roles for the amino protective groups, ring closure by olefin metathesis, face selective dihydroxylation, cyclic sulfate formation and finally opening with azide. The resulting 2-deoxystreptamine derivative is ideally protected for the preparation of 4,5- or 4,6-linked aminoglycoside antibiotics. (C) 2004 Elsevier Ltd. All rights reserved.