Premium
Pd‐Catalyzed Enantiodivergent and Regiospecific phospha ‐Michael Addition of Diphenylphosphine to 4‐ oxo ‐Enamides: Efficient Access to Chiral Phosphinocarboxamides and Their Analogues
Author(s) -
Chew Renta Jonathan,
Li XiRui,
Li Yongxin,
Pullarkat Sumod A.,
Leung PakHing
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406298
Subject(s) - stereoselectivity , diphenylphosphine , enantiomer , michael reaction , catalysis , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , phosphine
Abstract The palladacycle‐catalyzed asymmetric PH 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.