Synthesis 2008(19): 3160-3166  
DOI: 10.1055/s-2008-1067257
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of Branched Cyclopentitols by Titanium(III)-Promoted Reductive Cyclization of 4-Oxiranylaldehydes and 4-Oxiranyl Ketones Derived from Hexoses

Jose Luis Chiara*, Sofía Bobo, Esther Sesmilo
Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain
Fax: +34(91)5644853; e-Mail: jl.chiara@iqog.csic.es;
Further Information

Publication History

Received 19 May 2008
Publication Date:
05 September 2008 (online)

Abstract

Titanocene chloride efficiently promotes the intramolecular reductive cross coupling of highly functionalized 4-oxiranyl­aldehydes and 4-oxiranyl ketones derived from readily available hexoses affording branched cyclopentitols with good stereoselectivity.

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