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Selective termination of a polyene cyclization by an internally situated allylsilane group

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
35
Issue
39
Identifiers
DOI: 10.1016/0040-4039(94)85355-x

Abstract

Abstract The cyclization of epoxides 6 and 7, incorporating the internally situated propenyl and allylsilane terminator groups respectively, has demonstrated that the allylsilane function is the far superior group for terminating the cyclization process, and does so in a highly efficient and selective manner. Thus, treatment of 6 with ( i-PrO)TiCl 3 afforded bicyclic alcohols 23 in 79–82% yield.

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