Can an adjacent stereocenter control selectivity in the palladium-catalyzed allylic substitution reaction? If the intermediate π-allyl palladium complex can undergo rapid inversion, the answer is yes (see reaction scheme). Starting from chiral 5-vinyloxazolidinones, trapping of intermediates 1 and 2, which are in a dynamic equilibrium, with nitrogen-containing nucleophiles leads to the quantitative formation of diamines as single diastereomers.
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Cook et al. (1999) studied this question.