Literature DB >> 17168611

Phase transfer catalyzed enantioselective Strecker reactions of alpha-amido sulfones with cyanohydrins.

Raquel P Herrera1, Valentina Sgarzani, Luca Bernardi, Francesco Fini, Daniel Pettersen, Alfredo Ricci.   

Abstract

A study into the use of a chiral phase-transfer catalyst in conjunction with acetone cyanohydrin to effect the enantioselective formation of alpha-amino nitriles from alpha-amido sulfones is described. This novel catalytic asymmetric Strecker reaction is analyzed with regard to the possible mechanistic basis.

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Year:  2006        PMID: 17168611     DOI: 10.1021/jo061566u

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  6 in total

1.  Structural study-guided development of versatile phase-transfer catalysts for asymmetric conjugate additions of cyanide.

Authors:  Brian A Provencher; Keith J Bartelson; Yan Liu; Bruce M Foxman; Li Deng
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-14       Impact factor: 15.336

2.  Asymmetric Protonation of Cumulenolates: Synthesis of Allenyl Aldehydes Facilitated by an Organomanganese Auxiliary.

Authors:  Animesh Roy; Bilal A Bhat; Salvatore D Lepore
Journal:  Org Lett       Date:  2016-02-29       Impact factor: 6.005

3.  Scalable organocatalytic asymmetric Strecker reactions catalysed by a chiral cyanide generator.

Authors:  Hailong Yan; Joong Suk Oh; Ji-Woong Lee; Choong Eui Song
Journal:  Nat Commun       Date:  2012       Impact factor: 14.919

4.  Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides.

Authors:  Stephen W Laws; Lucas C Moore; Michael J Di Maso; Q Nhu N Nguyen; Dean J Tantillo; Jared T Shaw
Journal:  Org Lett       Date:  2017-05-05       Impact factor: 6.005

5.  Highly Enantioselective Asymmetric Darzens Reactions with a Phase Transfer Catalyst.

Authors:  Yan Liu; Brian A Provencher; Keith J Bartleson; Li Deng
Journal:  Chem Sci       Date:  2011-07       Impact factor: 9.825

6.  Synthesis of main-chain chiral quaternary ammonium polymers for asymmetric catalysis using quaternization polymerization.

Authors:  Naoki Haraguchi; Parbhej Ahamed; Md Masud Parvez; Shinichi Itsuno
Journal:  Molecules       Date:  2012-06-19       Impact factor: 4.411

  6 in total

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