Literature DB >> 12733893

Catalytic enantioselective Strecker reaction of ketoimines.

Shuji Masumoto1, Hiroyuki Usuda, Masato Suzuki, Motomu Kanai, Masakatsu Shibasaki.   

Abstract

A new method for the catalytic enantioselective Strecker reaction (cyanation) of N-diphenylphosphinoyl ketoimines is described. The asymmetric catalyst is a chiral gadolinium complex prepared from Gd(OiPr)3 and the d-glucose-derived ligand 3 in a 1:2 ratio. The reaction has a broad substrate generality, giving high enantioselectivity from aromatic, ethyl, primary alkyl, and alpha,beta-unsaturated ketoimines. The products could be easily converted to disubstituted alpha-amino acids and their derivatives.

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Year:  2003        PMID: 12733893     DOI: 10.1021/ja034980+

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  15 in total

1.  Enantioselective reduction of ketones and imines catalyzed by (CN-box)Re(V)-oxo complexes.

Authors:  Kristine A Nolin; Richard W Ahn; Yusuke Kobayashi; Joshua J Kennedy-Smith; F Dean Toste
Journal:  Chemistry       Date:  2010-08-16       Impact factor: 5.236

2.  Catalytic Enantioselective Electrophilic Aminations of Acyclic α-Alkyl β-Carbonyl Nucleophilies.

Authors:  Xiaofeng Liu; Bingfeng Sun; Li Deng
Journal:  Synlett       Date:  2009-06       Impact factor: 2.454

3.  Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine.

Authors:  Cedric L Hugelshofer; Kevin T Mellem; Andrew G Myers
Journal:  Org Lett       Date:  2013-06-07       Impact factor: 6.005

4.  Practical asymmetric amine nucleophilic approach for the modular construction of protected α-quaternary amino acids.

Authors:  Teng Liu; Shaofei Ni; Wusheng Guo
Journal:  Chem Sci       Date:  2022-06-05       Impact factor: 9.969

5.  Ag-catalyzed diastereo- and enantioselective vinylogous Mannich reactions of alpha-ketoimine esters. Development of a method and investigation of its mechanism.

Authors:  Laura C Wieland; Erika M Vieira; Marc L Snapper; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-01-21       Impact factor: 15.419

6.  Asymmetric synthesis of beta,gamma-unsaturated alpha-amino acids via efficient kinetic resolution with cinchona alkaloids.

Authors:  Jianfeng Hang; Li Deng
Journal:  Bioorg Med Chem Lett       Date:  2009-04-05       Impact factor: 2.823

7.  Catalytic asymmetric addition of diorganozinc reagents to N-phosphinoylalkylimines.

Authors:  Alexandre Côté; Alessandro A Boezio; André B Charette
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-02       Impact factor: 11.205

8.  Imitating prebiotic homochirality on Earth.

Authors:  Ronald Breslow; Mindy Levine; Zhan-Ling Cheng
Journal:  Orig Life Evol Biosph       Date:  2009-11-13       Impact factor: 1.950

9.  Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products.

Authors:  Makoto Shimizu; Miki Mushika; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2019-07-29       Impact factor: 4.036

Review 10.  Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams.

Authors:  Katherine M Byrd
Journal:  Beilstein J Org Chem       Date:  2015-04-23       Impact factor: 2.883

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