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

doi:10.1016/S0040-4039(97)01124-6

Tetrahedron Letters

Volume 38, Issue 29, 21 July 1997, Pages 5189-5192

https://doi.org/10.1016/S0040-4039(97)01124-6 Get rights and content

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

Abstract

J. Chem. Soc., Chem. Comun.

Tetrahedron Lett.

J. Org. Chem.

Tetrahedron Lett.

Chemtracts. Org. Chem.

Organometallics

Org. Synth.