Peterson olefination

Related to the Wittig reaction is the Peterson olefination.

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.

When the α-silyl carbanion contains electron-withdrawing substituents, the Peterson olefination directly forms the alkene.

The favorable formation of Si-O bonds drive many organic reactions such as the Brook rearrangement and Peterson olefination.

The C10 fragment was then introduced by the lithium salt of Trimethyl(phenylthiomethyl)silane 1.16 in a Peterson olefination to the sulfide 1.17 followed by deprotection to completed ring A 1.18.

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.

A wide variety of carbonyl olefination methods that are direct alternative to the Julia olefination are known: the Wittig reaction, the Horner-Wadsworth-Emmons reaction, Peterson olefination, and others.

When the α-silyl carbanion contains only alkyl, hydrogen, or electron-donating substituents, the stereochemical outcome of the Peterson olefination can be controlled, because at low temperature the elimination is slow and the intermediate β-hydroxysilane can be isolated.