Synthesis of Substituted Tetrahydropyrans via Intermolecular Reactions of δ-Halocarbanions with Aldehydes
Michał Barbasiewicz, Aneta Brud, Mieczysław Mąkosza*
*Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka
44/52, P. O. Box 58, 01-224 Warsaw 42, Poland, Email: icho-s
icho.edu.pl
M. Barbasiewicz, A. Brud, M. Mąkosza, Synthesis, 2007, 1209-1213.
DOI: 10.1055/s-2007-965972
Abstract
Cyclization of δ-halocarbanions to cyclobutanes is a relatively slow process, thus formation of tetrahydropyran derivatives via addition to aldehydes and subsequent cyclization is possible in high yield. A simple mechanistic discussion, optimization of the reaction conditions, and the scope of the reaction are discussed.
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Key Words
aldol reactions, sulfones, halocarbanions, cyclizations, tetrahydropyrans
ID: J66-Y2007-1210
