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Electrophile-induced cyclizations of silyl-substituted 4-alken-1-ols

✍ Scribed by Adiwidjaja, Gunadi ;Flörke, H. ;Kirschning, A. ;Schauman, Ernst

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 855 KB
Volume: 1995
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199519950369

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✦ Synopsis

Abstract

Silyl‐substituted 4‐alken‐1‐ols cyclize in the presence of a wide range of electrophilic reagents to give substituted tetra‐hydrofurans. The silyl group accelerates ring closure by its β‐effect and its position determines the efficiency of stereo‐control. Thus, a vinylic silyl group as in 1, 3‐9 gives mixtures of 2,5‐disubstituted tetrahydrofurans 2, 10‐21, favoring formation of the trans isomer. In contrast, an allylic silyl group as in 28‐30 exerts a high degree of stereocontrol, generally affording 2,3‐trans‐disubstituted tetrahydrofurans 31‐36.

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