Organocatalytic Domino Michael-Aldol
Reaction of Ketones and α,β-Unsaturated
Trifluoromethyl Ketones

Xiao-Jin Wang; Yan Zhao; Jin-Tao Liu

doi:10.1055/s-0028-1083255

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Synthesis 2008(24): 3967-3973
DOI: 10.1055/s-0028-1083255

PAPER

Organocatalytic Domino Michael-Aldol Reaction of Ketones and α,β-Unsaturated Trifluoromethyl Ketones

Xiao-Jin Wang, Yan Zhao, Jin-Tao Liu*
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: jtliu@mail.sioc.ac.cn;

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Publication History

Received 4 August 2008
Publication Date:
01 December 2008 (online)

Abstract
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Abstract

Pyrrolidine-catalyzed domino Michael-aldol reaction of α,β-unsaturated trifluoromethyl ketones and ketones was achieved under mild conditions; β-hydroxy-β-trifluoromethyl cyclohexanones were obtained in high yields with good diastereoselectivities.

Key words

bicyclic compounds - cyclizations - domino reactions - organocatalytic - trifluoromethyl

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Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 619907 (2a), CCDC 665816 (2m) and CCDC 665817 (2r). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].