Literature DB >> 25338974

Chiral ammonium betaine-catalyzed highly stereoselective aza-henry reaction of α-aryl nitromethanes with aromatic N-Boc imines.

Daisuke Uraguchi1, Keigo Oyaizu, Haruhiro Noguchi, Takashi Ooi.   

Abstract

A highly stereoselective aza-Henry reaction of α-aryl nitromethanes with aromatic N-Boc imines was established by using C1 -symmetric chiral ammonium betaine as a bifunctional organic base catalyst. Various substituted aryl groups for both imines and nitromethanes were tolerated in the reaction, and a series of precursors for the synthesis of unsymmetrical anti-1,2-diaryl ethylenediamines was provided.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric synthesis; aza-Henry reaction; betaines; organocatalysis; α-aryl nitromethane

Year:  2014        PMID: 25338974     DOI: 10.1002/asia.201402943

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  4 in total

1.  Enantioselective Addition of Bromonitromethane to Aliphatic N-Boc Aldimines Using a Homogeneous Bifunctional Chiral Organocatalyst.

Authors:  Kenneth E Schwieter; Jeffrey N Johnston
Journal:  ACS Catal       Date:  2015       Impact factor: 13.084

2.  Cinchonium Betaines as Efficient Catalysts for Asymmetric Proton Transfer Catalysis: The Development of a Practical Enantioselective Isomerization of Trifluoromethyl Imines.

Authors:  Xiao Zhou; Yongwei Wu; Li Deng
Journal:  J Am Chem Soc       Date:  2016-09-09       Impact factor: 15.419

3.  Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles.

Authors:  Masahiro Torii; Kohsuke Kato; Daisuke Uraguchi; Takashi Ooi
Journal:  Beilstein J Org Chem       Date:  2016-09-28       Impact factor: 2.883

4.  Fluorine-induced diastereodivergence discovered in an equally rare enantioselective syn-aza-Henry reaction.

Authors:  Jade A Bing; Nathan D Schley; Jeffrey N Johnston
Journal:  Chem Sci       Date:  2022-02-14       Impact factor: 9.825

  4 in total

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