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Asymmetric Reduction of Ketones by Phosphoric Acid Derived Catalysts
Author(s) -
Zhang Zuhui,
Jain Pankaj,
Antilla Jon C.
Publication year - 2011
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.201103883
Subject(s) - phosphoric acid , reduction (mathematics) , catalysis , chemistry , organic chemistry , mathematics , geometry
A new path to chiral alcohols : Asymmetric reduction of ketones was achieved utilizing a chiral Brønsted acid as precatalyst for the first time. Using catecholborane as the reducing agent, a highly enantioselective formation of chiral secondary alcohols was found with a broad substrate scope. Mechanistic studies indicate that phosphoryl catechol borate derived from the reaction of the Brønsted acid with catecholborane produced the active catalyst (see scheme).