Stille Coupling of Stereochemically Defined α-Sulfonamidoorganostannanes
- 11 November 2004
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (48) , 15666-15667
- https://doi.org/10.1021/ja044354s
Abstract
Addition of tributylstannylmetallics to (R)-tert-butanesulfonimine derivatives of arylaldehydes provides alpha-sulfinamidostannanes with high (>98% de) diastereoselectivities. Oxidation of these compounds with m-CPBA gives alpha-sulfonamidostannanes which undergo Pd/Cu-catalyzed Stille-type couplings with benzoyl chloride. Best yields are achieved using the electron-rich tris(2,4,6-trimethoxyphenyl)phosphine as the ligand. Inversion of configuration at the benzylic carbon is observed.Keywords
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