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Contents Vol 64(8)

Enabling the Development of N-Heterocyclic Carbene (NHC) Catalyzed Reactions: Practical Methods for the Preparation of 1-Acyl-2-Alkylcycloalkenes from Cycloalkanones

Sarah J. Ryan A , Lisa Candish A , Iván Martínez A and David W. Lupton A B
+ Author Affiliations
- Author Affiliations

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

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

Australian Journal of Chemistry 64(8) 1148-1157 https://doi.org/10.1071/CH11183
Submitted: 5 May 2011  Accepted: 10 June 2011   Published: 19 August 2011

Abstract

The synthesis of 1-acyl-2-alkylcycloalkenes from a variety of cycloalkanones has been achieved via either β-keto enol phosphates or β-bromoenones. Both methods exploit simple and readily scalable transformations allowing the preparation of the desired compounds to be achieved in three, or four steps, respectively. The utility of these strategies has been examined, resulting in the preparation of 17 disubstituted cycloalkenes.


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