Literature DB >> 26213807

γ-Carbon Activation through N-Heterocyclic Carbene/Brønsted Acids Cooperative Catalysis: A Highly Enantioselective Route to δ-Lactams.

Yonglong Xiao1,2, Jinxin Wang2, Wenjing Xia1, Shuangjie Shu1, Shenchao Jiao1, Yu Zhou1, Hong Liu1.   

Abstract

A γ-carbon activation method that operates through N-heterocyclic carbene/Brønsted acid cooperative catalysis for highly enantioselective synthesis of δ-lactams is reported. The protocol allows the challenging remote γ-carbon control of regioselectivity and enantioselectivity through introduction of an appropriate γ-leaving group in the enals. The reaction offers good yields and excellent enantioselectivities, and the resulting cyclic products can be easily converted into high-value drug-like derivatives.

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Year:  2015        PMID: 26213807     DOI: 10.1021/acs.orglett.5b01827

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


  2 in total

Review 1.  Recent advances of N-heterocyclic carbenes in the applications of constructing carbo- and heterocyclic frameworks with potential biological activity.

Authors:  Mei-Mei Li; Xiaozhen Chen; Yun Deng; Jun Lu
Journal:  RSC Adv       Date:  2021-11-26       Impact factor: 4.036

2.  Palladium-Catalyzed Enantioselective Relay Heck Arylation of Enelactams: Accessing α,β-Unsaturated δ-Lactams.

Authors:  Qianjia Yuan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2018-05-16       Impact factor: 15.419

  2 in total

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