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RESEARCH ARTICLE
Contents Vol 70(4)

N-Heterocyclic Carbene-Catalysed Mukaiyama–Michael Reaction and Mukaiyama Aldol/Mukaiyama–Michael Three-Component Coupling Reaction*

Kim Nguyen A and David W. Lupton A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry, Monash University, Clayton 3800, Vic., Australia.

B Corresponding author. Email: david.lupton@monash.edu

Australian Journal of Chemistry 70(4) 436-441 https://doi.org/10.1071/CH16566
Submitted: 5 October 2016  Accepted: 30 November 2016   Published: 20 January 2017

Abstract

An N-heterocyclic carbene-catalysed Mukaiyama–Michael addition between several trimethylsilyl (TMS) enol ethers and chalcone derivatives has been discovered. In addition, a related reaction cascade involving dehydrative Mukaiyama aldol followed by a Mukaiyama–Michael addition process has been developed. The later reaction can also be achieved as a three-component coupling reaction. The enantioselective variant of these reactions has been examined with homochiral catalysts. Though these catalysts were active, they fail to achieve enantioinduction.


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