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

Organic LettersPublished 30 May 2014
Jianfeng Xu, Chengli Mou, Tingshun Zhu, Bao-An Song, Yonggui Robin
Citations105
SJR quartileQ1
SJR score1.24
SNIP1.03

TL;DR

A chemo- and enantioselective cross-aza-benzoin reaction between enals and isatin-derived ketimines is disclosed, enabling the high chemoselectivity of the acyl anion reaction over enal α- and β-carbon reactions.

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.

Keywords

Chemistry