The Mechanism and an Improved Asymmetric Allylboration of Ketones Catalyzed by Chiral Biphenols | Zendy

Barnett David S. | Zendy; Moquist Philip N. | Zendy; Schaus Scott E. | Zendy

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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.

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