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

Zhenzhen Zhang, Yongna Zhang, Hui‐Xin Duan, Zhuofei Deng, You‐Qing Wang

2020Chemical Communications28 citationsDOI

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.

Topics & Concepts

Enantioselective synthesisCarbeneCycloadditionSulfonylChemistryCatalysisTrifluoromethylMedicinal chemistryStereochemistryOrganic chemistryAlkylN-Heterocyclic Carbenes in Organic and Inorganic ChemistryFluorine in Organic ChemistryCyclopropane Reaction Mechanisms
Enantioselective (3+2) cycloaddition <i>via</i> N-heterocyclic carbene-catalyzed addition of homoenolates to cyclic <i>N</i>-sulfonyl trifluoromethylated ketimines: synthesis of fused N-heterocycle γ-lactams | Litcius