Pd-catalyzed enantiodivergent and regiospecific phospha-michael addition of diphenylphosphine to 4-oxo-enamides : efficient access to chiral phosphinocarboxamides and their analogues

Abstract

The palladacycle-catalyzed asymmetric P-H addition of 4-oxo-enamides has been developed, which provides efficient access to phosphinocarboxamides and their analogues. Solvent-mediated reversal of stereoselectivity (ee from +96 % to −92 %) was observed, and the underlying mechanism that allows facile access to both enantiomers of the product by judicious choice of solvents is revealed.