Synthesis 2002(7): 0958-0972
DOI: 10.1055/s-2002-28506
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Tandem Ene-Reaction/Intramolecular Sakurai Cyclisation (IMSC): A Novel Access to Polysubstituted Tetrahydropyrans and γ-Butyrolactones Using a Unique Allylation Strategy

István E. Markó*, Raphaël Dumeunier, Cédric Leclercq, Bernard Leroy, Jean-Marc Plancher, Abdelaziz Mekhalfia, Daniel J. Bayston
Université catholique de Louvain, Département de Chimie, Unité de Chimie Organique et Médicinale, Bâtiment Lavoisier, Place Louis Paste­ur 1, 1348 Louvain-la-Neuve, Belgium
Fax: +32(10)478033; e-Mail: marko@chim.ucl.ac.be;
Further Information

Publication History

Received 11 April 2002
Publication Date:
14 May 2002 (online)

Abstract

The ene-reaction between a variety of aldehydes and allylsilane 22 generates highly functionalised homoallylic alcohols 23. These adducts undergo a subsequent Intramolecular Sakurai Cyclisation (IMSC), affording in good yields polysubstituted tetrahydropyran derivatives. Furthermore, oxidative desilylation of 23 provides an efficient, connective access to a range of γ-butyrolactones and α-methylene-γ-butyrolactones.