Global InformationOrganostannane addition information
Organostannane addition reactions comprise the nucleophilic addition of an allyl-, allenyl-, or propargylstannane to an aldehyde, imine, or, in rare cases, a ketone.[1] The reaction is widely used for carbonyl allylation.
Organostannane addition to carbonyl groups constitutes one of the most common and efficient methods for the construction of contiguous, oxygen-containing stereocenters in organic molecules. As many molecules containing this motif—polypropionates and polyacetates, for instance—are desired by natural products chemists, the title reaction has become important synthetically and has been heavily studied over the years.[2][3] Substituted allylstannanes may create one or two new stereocenters, often with a very high degree of stereocontrol.
(1)
Organostannanes are known for their stability, ease of handling, and selective reactivity. Chiral allylstannanes often react with good stereoselectivity to give single diastereomers. Models explaining the sense of selectivity are reliable. In terms of disadvantages, stoichiometric amounts of metal-containing byproducts are generated. Additions to sterically encumbered pi bonds, such as those of ketones, are uncommon.
- ^ Gung, B. W. Org. React. 2004, 64, 1-112. doi:10.1002/0471264180.or064.01
- ^ Denmark, S. E.; Weber, E. J. J. Am. Chem. Soc. 1984, 106, 7970.
- ^ Keck, G. E.; Dougherty, S. M.; Savin, K. A. J. Am. Chem. Soc. 1995, 117, 6210.