An N-heterocyclic carbene-catalyzed enantioselective [3 + 2] annulation of enals with propargylic imines: access to γ,γ-disubstituted pyrrolidin-2-ones bearing quaternary stereogenic centers

Jianming Zhang; Zheng Liang; Simiao Zhang; Lei Chen; Xiaoxue Wang; Yuchan Wang; Jie Feng; Tao Lu; Ding Du; Jian Gao

doi:10.1039/D2QO00350C

An N-heterocyclic carbene-catalyzed enantioselective [3 + 2] annulation of enals with propargylic imines: access to γ,γ-disubstituted pyrrolidin-2-ones bearing quaternary stereogenic centers†

Jianming Zhang,‡^a Zheng Liang,‡^a Simiao Zhang,^a Lei Chen,^a Xiaoxue Wang,^a Yuchan Wang,^a Jie Feng,

^a Tao Lu,*^a Ding Du

*^a and Jian Gao

*^a

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* Corresponding authors

^a Department of Chemistry, State Key Laboratory of Natural Medicines, China Pharmaceutical University, P. R. China
E-mail: lut163@163.com, ddmn9999@cpu.edu.cn, gaojian@cpu.edu.cn

Abstract

An N-heterocyclic carbene-catalyzed asymmetric [3 + 2] annulation of enals with propargylic ketimines for the facile and enantioselective construction of γ,γ-disubstituted pyrrolidin-2-ones has been developed. This potocol was featured with mild reaction conditions, wild functional group tolerance, easy scalability, and high level of enantioselectivity, which also enriched the chemistry of NHC-bound homoenolates involved synthesis of γ-lactams bearing γ-quaternary stereogenic centers from acyclic kitimimes.

Organic Chemistry Frontiers

An N-heterocyclic carbene-catalyzed enantioselective [3 + 2] annulation of enals with propargylic imines: access to γ,γ-disubstituted pyrrolidin-2-ones bearing quaternary stereogenic centers†

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An N-heterocyclic carbene-catalyzed enantioselective [3 + 2] annulation of enals with propargylic imines: access to γ,γ-disubstituted pyrrolidin-2-ones bearing quaternary stereogenic centers

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