Literature DB >> 19583199

Diastereo- and enantioselective Aza-MBH-type reaction of nitroalkenes to N-tosylimines catalyzed by bifunctional organocatalysts.

Xiao Wang1, Yong-Fei Chen, Liang-Feng Niu, Peng-Fei Xu.   

Abstract

The first example of diastereo- and enantioselective aza-MBH-type reaction was accomplished by the asymmetric synthesis of beta-nitro-gamma-enamines via a (1R,2R)-diaminocyclohexane thiourea derivative mediated tandem Michael addition and aza-Henry reaction in good yields (up to 95%) and high enantioselectivities (up to 91% ee) and diastereoselectivities (up to 1:99 dr).

Entities:  

Year:  2009        PMID: 19583199     DOI: 10.1021/ol9011458

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


  3 in total

1.  DFT-Based Stereochemical Rationales for the Bifunctional Brønsted Acid/Base-Catalyzed Diastereodivergent and Enantioselective aza-Henry Reactions of α-Nitro Esters.

Authors:  Thomas J Struble; Ivor Smajlagic; Hayden Foy; Travis Dudding; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2021-10-20       Impact factor: 4.354

Review 2.  Enantioselective, organocatalytic Morita-Baylis-Hillman and Aza-Morita-Baylis-Hillman reactions: stereochemical issues.

Authors:  Javier Mansilla; José M Saá
Journal:  Molecules       Date:  2010-02-01       Impact factor: 4.411

3.  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

  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.