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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

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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


Submitted
28 Nov 2019
Accepted
03 Jan 2020
First published
04 Jan 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

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, Advance Article , DOI: 10.1039/C9CC09269B

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