Issue 24, 2011

An organocatalytic approach to enantiomerically enriched α-arylcyclohexenones and cyclohexanones

Abstract

The presence of a p-nitrophenyl group converts acetone into an excellent and versatile nucleophile in organocatalytic processes, able to react with α,β-unsaturated aldehydes affording β-substituted α-arylcyclohexenones via a Michael reaction/aldol reaction/dehydration sequence, which occurs in good yields, ee up to 96% and complete diastereoselectivity. The resulting compounds are excellent synthons for the diastereoselective preparation of a variety of synthetically useful polysubstituted cyclohexanones and derivatives.

Graphical abstract: An organocatalytic approach to enantiomerically enriched α-arylcyclohexenones and cyclohexanones

Supplementary files

Article information

Article type
Paper
Submitted
09 Aug 2011
Accepted
01 Sep 2011
First published
01 Nov 2011

Org. Biomol. Chem., 2011,9, 8253-8260

An organocatalytic approach to enantiomerically enriched α-arylcyclohexenones and cyclohexanones

S. Duce, M. Jorge, I. Alonso, J. L. G. Ruano and M. B. Cid, Org. Biomol. Chem., 2011, 9, 8253 DOI: 10.1039/C1OB06356A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements