PAPER	Synthesis 2005: 2297-2306   DOI: 10.1055/s-2005-872091
© 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
Received 2 October 2004

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