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γ-Regioselective reaction of metaloxysilyl-substituted allyllithium derived from allyldiphenylsilanol

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
38
Issue
29
Identifiers
DOI: 10.1016/s0040-4039(97)01124-6

Abstract

Abstract Treatment of allyldiphenylsilanol ( 1) with two equivalents of butyllithium in the presence of HMPA at −45°C afforded silylallyllithium 2a bearing an oxide anion on the silicon atom. The reaction of 2a with various electrophiles gave γ-products selectively in good yields. Higher regio- and stereoselectivities were achieved in the reaction of silyl-substituted allyllithium derived from potassium allylsilanolate with butyllithium.

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