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Literature DB >> 20161386

Asymmetric synthesis of (2S,3R)-(-)-epi-CP-99,994 using sulfinimine-derived anti-2,3-diamino esters.

Abstract

A differentially protected C-3 N-sulfinyl, C-2 N,N-(diphenylmethylene) 2,3-diamino ester was employed in the synthesis of the amino piperidine (2S,3R)-(-)-epi-CP-99,994. Key steps in the synthesis included the chemoselective hydrolysis of the C-2 N,N-(diphenylmethylene) group and its reprotection as a dibenzylamino group.

Entities: Chemical Disease Species

Year: 2009 PMID： 20161386 PMCID： PMC2782829 DOI： 10.1016/j.tetlet.2009.06.125

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

13 in total

Review 1. Alpha,beta-diamino acids: biological significance and synthetic approaches.

Authors: Alma Viso; Roberto Fernández de la Pradilla; Ana García; Aida Flores
Journal: Chem Rev Date: 2005-08 Impact factor: 60.622

2. Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures(1).

Authors: Ahmed F. Abdel-Magid; Kenneth G. Carson; Bruce D. Harris; Cynthia A. Maryanoff; Rekha D. Shah
Journal: J Org Chem Date: 1996-05-31 Impact factor: 4.354

3. Asymmetric synthesis of ring functionalized trans-2,6-disubstituted piperidines from N-sulfinyl delta-amino beta-keto phosphonates. total synthesis of (-)-myrtine.

Authors: Franklin A Davis; He Xu; Junyi Zhang
Journal: J Org Chem Date: 2007-02-17 Impact factor: 4.354

Review 4. Adventures in sulfur-nitrogen chemistry.

Authors: Franklin A Davis
Journal: J Org Chem Date: 2006-11-24 Impact factor: 4.354

Review 5. Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry.

Authors: S R S Saibabu Kotti; Cody Timmons; Guigen Li
Journal: Chem Biol Drug Des Date: 2006-02 Impact factor: 2.817

6. A direct stereoselective approach to trans-2,3-disubstituted piperidines: application in the synthesis of 2-Epi-CP-99,994 and (+)-epilupinine.

Authors: M'hamed Ahari; Amandine Perez; Christine Menant; Jean-Luc Vasse; Jan Szymoniak
Journal: Org Lett Date: 2008-05-14 Impact factor: 6.005

7. Asymmetric synthesis of syn-(2R,3S)-and anti-(2S,3S)-ethyl diamino-3-phenylpropanoates from N-(benzylidene)-p-toluenesulfinamide and glycine enolates.

Authors: Franklin A Davis; Jianghe Deng
Journal: Org Lett Date: 2004-08-05 Impact factor: 6.005

3. Asymmetric synthesis of γ-chloro-α,β-diamino- and β,γ-aziridino-α-aminoacylpyrrolidines and -piperidines via stereoselective Mannich-type additions of N-(diphenylmethylene)glycinamides across α-chloro-N-sulfinylimines.

Authors: Gert Callebaut; Sven Mangelinckx; Pieter Van der Veken; Karl W Törnroos; Koen Augustyns; Norbert De Kimpe
Journal: Beilstein J Org Chem Date: 2012-12-05 Impact factor: 2.883

3 in total

Asymmetric synthesis of (2S,3R)-(-)-epi-CP-99,994 using sulfinimine-derived anti-2,3-diamino esters.

Review 1. Alpha,beta-diamino acids: biological significance and synthetic approaches.

2. Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures(1).

3. Asymmetric synthesis of ring functionalized trans-2,6-disubstituted piperidines from N-sulfinyl delta-amino beta-keto phosphonates. total synthesis of (-)-myrtine.

Review 4. Adventures in sulfur-nitrogen chemistry.

Review 5. Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry.

6. A direct stereoselective approach to trans-2,3-disubstituted piperidines: application in the synthesis of 2-Epi-CP-99,994 and (+)-epilupinine.

7. Asymmetric synthesis of syn-(2R,3S)-and anti-(2S,3S)-ethyl diamino-3-phenylpropanoates from N-(benzylidene)-p-toluenesulfinamide and glycine enolates.

8. Synthesis of highly substituted enantiopure piperazines and ketopiperazines from vicinal N-sulfinyl diamines.

9. Sulfinimine-derived 2,3-diamino esters in the asymmetric synthesis of piperidine (2S,3S)-(+)-CP-99,994.

10. Fine-tuned aminal cleavage: a concise route to differentially protected enantiopure syn-alpha,beta-diamino Esters.

1. A Highly Divergent Synthesis of 3-Aminotetrahydropyridines.

Review 2. Applications of aryl-sulfinamides in the synthesis of N-heterocycles.

3. Asymmetric synthesis of γ-chloro-α,β-diamino- and β,γ-aziridino-α-aminoacylpyrrolidines and -piperidines via stereoselective Mannich-type additions of N-(diphenylmethylene)glycinamides across α-chloro-N-sulfinylimines.