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4.4.37 Product Subclass 37: β-Silyl Alcohols and the Peterson Reaction

DOI: 10.1055/sos-SD-004-00846

Ager, D. J.Science of Synthesis, (20024789.

General Introduction

β-Silyl alcohols 1 are useful reagents, principally as precursors to alkenes, and are often isolated as such. The elimination of the silicon moiety and oxygen, when no electron-withdrawing group is present on the carbon bearing the silicon, can be controlled in a stereoselective manner. This reaction has been called the Peterson alkenation reaction.[‌1‌‌3‌] The mode of elimination can be controlled by the use of acid or base (Scheme 1).[‌4‌,‌5‌] If an electron-withdrawing group is present on the carbon atom that is bonded to silicon, then the β-hydroxysilane cannot usually be isolated, as the elimination to provide the alkene is rapid under the reaction conditions. The CC bond-forming step is usually under kinetic control and mixtures of alkene isomers can result when the base mode of elimination occurs under the basic reaction conditions.[‌2‌,‌3‌] This can be an advantage compared to the Wittig reaction and its variants which, although proceeding with high stereoselection, may only provide access to the thermodynamically more stable alkene.[‌2‌]

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