Literature DB >> 10754676

(S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones: ideal Michael acceptors to afford a virtually complete control of simple and face diastereoselectivity in addition reactions with glycine derivatives.

V A Soloshonok1, C Cai, V J Hruby.   

Abstract

[formula: see text] Enantiomerically pure (S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones were found to serve as ideal Michael acceptors in addition reactions with achiral Ni(II) complexes of glycine Schiff bases. Virtually complete control of simple and face diastereoselectivity, observed in these reactions, combined with quantitative chemical yields renders this methodology synthetically superior to the previous methods.

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Year:  2000        PMID: 10754676     DOI: 10.1021/ol990402f

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


  8 in total

1.  Michael addition reactions between chiral equivalents of a nucleophilic glycine and (S)- or (R)-3-[(E)-enoyl]-4-phenyl-1,3-oxazolidin-2-ones as a general method for efficient preparation of beta-substituted pyroglutamic acids. Case of topographically controlled stereoselectivity.

Authors:  Vadim A Soloshonok; Chaozhong Cai; Takeshi Yamada; Hisanori Ueki; Yasufumi Ohfune; Victor J Hruby
Journal:  J Am Chem Soc       Date:  2005-11-02       Impact factor: 15.419

2.  Enhanced stereoselectivity of a Cu(II) complex chiral auxiliary in the synthesis of Fmoc-L-γ-carboxyglutamic acid.

Authors:  Daniel J Smith; Glenn P A Yap; James A Kelley; Joel P Schneider
Journal:  J Org Chem       Date:  2011-02-03       Impact factor: 4.354

Review 3.  Organic chemistry and biology: chemical biology through the eyes of collaboration.

Authors:  Victor J Hruby
Journal:  J Org Chem       Date:  2009-12-18       Impact factor: 4.354

Review 4.  Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs.

Authors:  Yi Zhu; Jianlin Han; Jiandong Wang; Norio Shibata; Mikiko Sodeoka; Vadim A Soloshonok; Jaime A S Coelho; F Dean Toste
Journal:  Chem Rev       Date:  2018-04-02       Impact factor: 60.622

Review 5.  Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids.

Authors:  Jianlin Han; Todd T Romoff; Hiroki Moriwaki; Hiroyuki Konno; Vadim A Soloshonok
Journal:  ACS Omega       Date:  2019-11-07

6.  Asymmetric Synthesis of 4,4-(Difluoro)glutamic Acid via Chiral Ni(II)-Complexes of Dehydroalanine Schiff Bases. Effect of the Chiral Ligands Structure on the Stereochemical Outcome.

Authors:  Yoshinori Tokairin; Yuhei Shigeno; Jianlin Han; Gerd-Volker Röschenthaler; Hiroyuki Konno; Hiroki Moriwaki; Vadim A Soloshonok
Journal:  ChemistryOpen       Date:  2020-01-29       Impact factor: 2.911

7.  Design and synthesis of quasi-diastereomeric molecules with unchanging central, regenerating axial and switchable helical chirality via cleavage and formation of Ni(II)-O and Ni(II)-N coordination bonds.

Authors:  Vadim A Soloshonok; José Luis Aceña; Hisanori Ueki; Jianlin Han
Journal:  Beilstein J Org Chem       Date:  2012-11-13       Impact factor: 2.883

8.  Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid.

Authors:  Jianlin Han; Ryosuke Takeda; Xinyi Liu; Hiroyuki Konno; Hidenori Abe; Takahiro Hiramatsu; Hiroki Moriwaki; Vadim A Soloshonok
Journal:  Molecules       Date:  2019-12-10       Impact factor: 4.411

  8 in total

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