A Powerful Chiral Phosphoric Acid Catalyst for Enantioselective Mukaiyama–Mannich Reactions | Zendy

Zhou Fengtao | Zendy; Yamamoto Hisashi | Zendy

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A Powerful Chiral Phosphoric Acid Catalyst for Enantioselective Mukaiyama–Mannich Reactions

Author(s) -

Zhou Fengtao,

Yamamoto Hisashi

Publication year - 2016

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201603929

Subject(s) - enantioselective synthesis , stereocenter , phosphoric acid , ketene , moiety , chemistry , catalysis , mannich reaction , organic chemistry , organocatalysis , silylation , vicinal , combinatorial chemistry

A new BINOL‐derived chiral phosphoric acid bearing 2,4,6‐trimethyl‐3,5‐dinitrophenyl substituents at the 3,3′‐positions was developed. The utility of this chiral phosphoric acid is demonstrated by a highly enantioselective ( ee up to >99 %) and diastereoselective ( syn / anti up to >99:1) asymmetric Mukaiyama–Mannich reaction of imines with a wide range of ketene silyl acetals. Moreover, this method was successfully applied to the construction of vicinal tertiary and quaternary stereogenic centers with excellent diastereo‐ and enantioselectivity. Significantly, BINOL‐derived N ‐triflyl phosphoramide constitutes a complementary catalyst system that allows the title reaction to be applied to more challenging imines without an N‐( 2‐hydroxyphenyl) moiety.

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