Peterson olefination

Peterson Olefination

Peterson olefination

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The Peterson olefination (also called the Peterson reaction) is the chemical reaction of α-silyl carbanions 1 with ketones (or aldehydes) to form a β-hydroxysilane 2 which eliminates to form alkenes 3.

Several reviews have been published.Birkofer, L.; Stiehl, O. Top. Curr. Chem. 1980, 88, 58. (Review)Ager, D. J. Synthesis 1984, 384-398. (Review)Ager, D. J. Org. React. 1990, 38, 1. (doi:)

Reaction mechanism

One attractive feature of the Peterson olefination is that it can be used to prepare either cis- or trans-alkenes from the same β-hydroxysilane. Treatment of the β-hydroxysilane with acid will yield one alkene, while treatment of the same β-hydroxysilane with base will yield the alkene of opposite stereochemistry.

Basic elimination

The action of base upon a β-hydroxysilane 1 results in a concerted syn elimination of 2 or 3 to form the desired alkene. The penta-coordinate silicon intermediate 3 is postulated, but no proof exists to date.

Potassium alkoxides eliminate quickly, while sodium alkoxides generally require heating. Magnesium alkoxides only eliminate in extreme conditions. The order of reactivity of alkoxides, K > Na >> Mg, is consistent with higher electron density on oxygen, hence increasing the...
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