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.
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Kells et al. (2004) studied this question.
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