Pd-Catalyzed Enantiodivergent and Regiospecific phospha-Michael Addition of Diphenylphosphine to 4- oxo-Enamides: Efficient Access to Chiral Phosphinocarboxamides and Their Analogues.

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. [ABSTRACT FROM AUTHOR]