Issue 10, 2020
From the journal:

Chemical Communications

Enantioselective (3+2) cycloaddition via N-heterocyclic carbene-catalyzed addition of homoenolates to cyclic N-sulfonyl trifluoromethylated ketimines: synthesis of fused N-heterocycle γ-lactams†

Zhen-Zhen Zhang,a   Yongna Zhang,*a   Hui-Xin Duan,a   Zhuo-Fei Denga  and  You-Qing Wang ORCID logo *a  

* Corresponding authors

a Henan Key Laboratory of Polyoxometalate Chemistry, Provincial Key Laboratory of Natural Medicine and Immuno-Engineering, and College of Chemistry and Chemical Engineering, Henan University, Kaifeng, Henan 475004, P. R. China
E-mail: zhangyongna@henu.edu.cn, wyouqing@hotmail.com

Abstract

An enantioselective (3+2) cycloaddition of enals and cyclic N-sulfonyl trifluoromethyl ketimines via N-heterocyclic carbene-catalyzed homoenolate addition is described. This reaction can efficiently construct fused N-heterocycle γ-lactams bearing two adjacent chiral centers with >20 : 1 dr and 94–99% ee, with one chiral center as a trifluoromethylated α-tetrasubstituted carbon stereocenter.

Graphical abstract: Enantioselective (3+2) cycloaddition via N-heterocyclic carbene-catalyzed addition of homoenolates to cyclic N-sulfonyl trifluoromethylated ketimines: synthesis of fused N-heterocycle γ-lactams

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Article information

DOI
https://doi.org/10.1039/C9CC09269B
Article type
Communication
Submitted
28 Nov 2019
Accepted
03 Jan 2020
First published
04 Jan 2020

Chem. Commun., 2020,56, 1553-1556

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Enantioselective (3+2) cycloaddition via N-heterocyclic carbene-catalyzed addition of homoenolates to cyclic N-sulfonyl trifluoromethylated ketimines: synthesis of fused N-heterocycle γ-lactams

Z. Zhang, Y. Zhang, H. Duan, Z. Deng and Y. Wang, Chem. Commun., 2020, 56, 1553 DOI: 10.1039/C9CC09269B

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