Literature DB >> 28703601

Enantioselective [3 + 2] Annulation of Enals with 2-Aminoacrylates Catalyzed by N-Heterocyclic Carbene.

Xing-Shuo Li1, Liang-Liang Zhao1, Xiao-Ke Wang1, Li Li Cao1, Xiao-Qian Shi1, Rui Zhang1, Jing Qi1.   

Abstract

A novel and convenient strategy for the enantioselective synthesis of γ-lactam derivatives via N-heterocyclic carbene catalyzed formal [3 + 2] annulation of enals with 2-aminoacrylates is disclosed. This activation mode provides a complementary approach to the synthesis of various γ-lactam derivatives in good yields with excellent diastereo- and enantioselectivities. In this process, two consecutive stereocenters are constructed, and a quaternary carbon center is also established.

Entities:  

Year:  2017        PMID: 28703601     DOI: 10.1021/acs.orglett.7b01860

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


  1 in total

1.  Enantioselective Michael-Proton Transfer-Lactamization for Pyroglutamic Acid Derivatives: Synthesis of Dimethyl-(S,E)-5-oxo-3-styryl-1-tosylpyrrolidine-2,2-dicarboxylate.

Authors:  Christian M Chaheine; Conner J Song; Paul T Gladen; Daniel Romo
Journal:  Organic Synth       Date:  2021
  1 in total

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