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

Chew Renta Jonathan | Zendy; Li XiRui | Zendy; Li Yongxin | Zendy; Pullarkat Sumod A. | Zendy; Leung PakHing | Zendy

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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

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.

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