| 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.[1][2][3] The reaction was discovered by Robert H. Shapiro in 1967.[4] The Shapiro reaction was used in the Nicolaou Taxol total synthesis.[5] This reaction is very similar to the Bamford–Stevens reaction, which also involves the basic decomposition of tosyl hydrazones.
- ^ Shapiro, R. H.; Lipton, M. F.; Kolonko, K. J.; Buswell, R. L.; Capuano, L. A. (1975). "Tosylhydrazones and alkyllithium reagents: More on the regiospecificity of the reaction and the trapping of three intermediates". Tetrahedron Lett. 16 (22–23): 1811–1814. doi:10.1016/S0040-4039(00)75263-4.
- ^ Shapiro, Robert H. (1976). "Alkenes from Tosylhydrazones". Org. React. 23 (3): 405–507. doi:10.1002/0471264180.or023.03. ISBN 978-0471264187.
- ^ Adlington, Robert M.; Barret, Anthony G. M. (1983). "Recent applications of the Shapiro reaction". Acc. Chem. Res. 16 (2): 55–59. doi:10.1021/ar00086a004.
- ^ Shapiro, Robert H.; Heath, Marsha J. (1967). "Tosylhydrazones. V. Reaction of Tosylhydrazones with Alkyllithium Reagents. A New Olefin Synthesis". J. Am. Chem. Soc. 89 (22): 5734–5735. doi:10.1021/ja00998a601.
- ^ Nicolaou, Kyriacos C.; Sorensen, Erik J. (1996). Classics in Total Synthesis: Targets, Strategies, Methods. Wiley. ISBN 9783527292318.