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The Mechanism and an Improved Asymmetric Allylboration of Ketones Catalyzed by Chiral Biphenols
Author(s) -
Barnett David S.,
Moquist Philip N.,
Schaus Scott E.
Publication year - 2009
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.200904715
Subject(s) - catalysis , mechanism (biology) , chemistry , combinatorial chemistry , organic chemistry , physics , quantum mechanics
Giving it a boost : A mechanistic study of the enantioselective asymmetric titled reaction with allyldiisopropoxyborane catalyzed by chiral biphenols revealed a key ligand exchange process which liberates isopropyl alcohol. The addition of i PrOH to the reaction increases the overall rate and enantioselectivity. As a result an improved reaction, employing allyldioxaborinane with 1 and t BuOH, resulted in high product yields and enantioselectivities.