N-Heterocyclic Carbene-Catalyzed Chemoselective Cross-Aza-Benzoin Reaction of Enals with Isatin-Derived Ketimines: Access to Chiral Quaternary Aminooxindoles

2014105 citationsJournal Article

Authors

Jianfeng Xu · Nanyang Technological University

Tingshun Zhu · Nanyang Technological University

Abstract

A chemo- and enantioselective cross-aza-benzoin reaction between enals and isatin-derived ketimines is disclosed. The high chemoselectivity (of the acyl anion reaction over enal α- and β-carbon reactions) is enabled by the electronic and steric properties of the N-heterocyclic carbene organocatalyst.

Topics & Keywords

N-Heterocyclic Carbenes in Organic and Inorganic Chemistry Asymmetric Hydrogenation and Catalysis Coordination Chemistry and Organometallics

UN Sustainable Development Goals

Clean water and sanitation

Publication Details

Published in: Organic Letters

Volume 16, Issue 12, pp. 3272-3275

DOI: 10.1021/ol501286e

Field-Weighted Citation Impact: 8.75