Shapiro reaction

Shapiro reaction
Named after Robert H. Shapiro
Reaction type Coupling reaction
Identifiers
Organic Chemistry Portal shapiro-reaction
RSC ontology ID RXNO:0000125

The Shapiro reaction or tosylhydrazone decomposition is an organic reaction in which a ketone or aldehyde is converted to an alkene through an intermediate hydrazone in the presence of 2 equivalents of organolithium reagent. The reaction was discovered by Robert H. Shapiro in 1967. The Shapiro reaction was used in the Nicolaou Taxol total synthesis. This reaction is very similar to the Bamford–Stevens reaction, which also involves the basic decomposition of tosyl hydrazones.

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