Literature DB >> 15281770

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

Franklin A Davis1, Jianghe Deng.   

Abstract

Addition of differentially N-protected glycine enolates to enantiopure sulfinimines affords syn- and anti-alpha,beta-diamino esters with high diastereoselectivities and good yields.

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Year:  2004        PMID： 15281770     DOI： 10.1021/ol048981y

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  5 in total

1.  The supersilyl group as a carboxylic acid protecting group: application to highly stereoselective aldol and Mannich reactions.

Authors:  Jiajing Tan; Matsujiro Akakura; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-29       Impact factor: 15.336

2.  Asymmetric synthesis of anti- and syn-2,3-diamino esters using sulfinimines. Water and concentration effects.

Authors:  Franklin A Davis; Yanfeng Zhang; Hui Qiu
Journal:  Org Lett       Date:  2007-01-30       Impact factor: 6.005

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

Authors:  Franklin A Davis; Yanfeng Zhang; Danyang Li
Journal:  Tetrahedron Lett       Date:  2007-10-29       Impact factor: 2.415

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

Authors:  Franklin A Davis; Yanfeng Zhang
Journal:  Tetrahedron Lett       Date:  2009-11-16       Impact factor: 2.415

5.  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
  5 in total

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