Addition of racemic alkoxyallylstannanes to an enantiomerically pure 2-methoxyoxazolidine: an example of combined mutual diastereoface selection and kinetic resolution

The BF 3 .Et 2 O-promoted addition of racemic α-and γ-alkoxyallylstannanes to 2-methoxyoxazolidine afforded adducts in diastereoisomeric ratios up to 95:5 accompoanied by enantioenriched γ-stannanes.The behavior is consistent with a fast α-to-γ rearrangement of the alkoxystannanes followed by an enantiomer- as well as mutual diastereoface-discriminating condensation