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Synthesis 2001(12): 1888-1896
DOI: 10.1055/s-2001-17511
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Pauson-Khand Cyclizations of 1-Sulfinylenynes

Juan Carlos Carretero*, Javier Adrio
a Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
Fax: +34(9)13973925; e-Mail: juancarlos.carretero@uam.es;
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Publication History

Received 21 May 2001
Publication Date:
11 August 2004 (online)

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Abstract

The use of sulfoxides as chiral auxiliaries in intramolecular Pauson-Khand (PK) reactions is described. In particular, the tert-butylsulfinyl group acts as a very efficient chiral auxiliary in intramolecular PK reactions of 1-sulfinyl-1,6-enynes. As the starting enynes are readily available in optically pure form and the final desulfinylation step is high yielding, this procedure constitutes an efficient alternative to the synthesis of enantiomerically pure bicyclo[3.3.0]oct-1-en-3-ones.

Key words

sulfoxides - Pauson-Khand reaction - asymmetric synthesis - enynes - bicyclo[3.3.0]octenones

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10

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