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Synthesis 2005(14): 2297-2306  
DOI: 10.1055/s-2005-872091
PAPER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Epoxidation of Allylic Diols Derived from Baylis-Hillman Adducts

Ricardo S. Portoa, Mario L. A. A. Vasconcellosb, Elizete Venturab, Fernando Coelho*a
a Laboratory of Synthesis of Natural Products and Drugs, Organic Chemistry Department, Chemistry Institute/Unicamp, PO Box 6154, 13084-971 Campinas SP, Brazil
Fax: +19(55)37883023; e-Mail: coelho@iqm.unicamp.br;
b Departamento de Química, Universidade Federal da Paraíba, João Pessoa, PB, Brazil
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Publication History

Received 2 October 2004
Publication Date:
20 July 2005 (online)

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Diastereoselective Epoxidation of Allylic Diols Derived from Baylis-Hillman AdductsSynthesis 2005; 2005(15): 2630-2630
DOI: 10.1055/s-2005-872161

Abstract

The results of a highly diastereoselective epoxidation of allylic diols derived from Baylis-Hillman adducts are reported. The formation of an intramolecular hydrogen bond seems to be responsible for the high anti diastereoselection obtained in this epoxidation reaction. The results are complementary to those obtained in the direct epoxidation of Baylis-Hillman adducts, in which an elevated syn diastereoselectivity was observed.

Key words

Baylis-Hillman reaction - epoxidation - allylic alcohol - silicon - diastereoselectivity