Issue 24, 2002
From the journal:

Chemical Communications

β-Hydroxysulfoxides as chiral cyclic ketone equivalents: enantioselective synthesis of polysubstituted cyclohexanones, cyclohexenones and cyclohexenediones†

M. Carmen Carreño,*a   Manuel Pérez-González,a   María Ribagorda,a   Álvaro Somozaa  and  Antonio Urbanoa  

* Corresponding authors

a Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain
E-mail: carmen.carrenno@uam.es

Abstract

The β-hydroxysulfoxide moiety, after oxidation to sulfone, acts as a masked carbonyl group in a cyclic system, opening an easy access to differently substituted enantiomerically pure cyclic ketones by means of aluminium-mediated conjugate additions, stereoselective reductions and elimination by retrocondensation in basic medium.

Graphical abstract: β-Hydroxysulfoxides as chiral cyclic ketone equivalents: enantioselective synthesis of polysubstituted cyclohexanones, cyclohexenones and cyclohexenediones

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Article information

DOI
https://doi.org/10.1039/B209121F
Article type
Communication
Submitted
17 Sep 2002
Accepted
28 Oct 2002
First published
18 Nov 2002

Chem. Commun., 2002, 3052-3053

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β-Hydroxysulfoxides as chiral cyclic ketone equivalents: enantioselective synthesis of polysubstituted cyclohexanones, cyclohexenones and cyclohexenediones

M. C. Carreño, M. Pérez-González, M. Ribagorda, Á. Somoza and A. Urbano, Chem. Commun., 2002, 3052 DOI: 10.1039/B209121F

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