A series of novel ?-hydroxyamide based catalysts for borane-mediated enantioselective reductions of prochiral ketones
[ X ]
Date
2016
Journal Title
Journal ISSN
Volume Title
Publisher
Pergamon-Elsevier Science Ltd
Access Rights
info:eu-repo/semantics/closedAccess
Abstract
The enantioselective reduction of prochiral ketones with borane in the presence of a chiral ligand has received considerable attention. Hydroxylamine-based chiral ligands with amide and hydroxyl functions in the presence of other co-ordinating groups are highly effective in these asymmetric reductions. The current work presents a simple one step synthesis of a series of beta-hydroxyamide-based ligands from the reaction between 3-hydroxy-2-naphthoic acid and chiral amino alcohols and their applications as catalysts in asymmetric borane-mediated reductions of aromatic prochiral ketones in THE The reductions provided the corresponding secondary alcohols with up to 96% ee and in good to excellent yields (89-99%). OFF calculations at B3LYP/6-31+g(d) level offered theoretical models to account for the enantioselectivity imposed by the chiral ligands in the reductions of the ketones. (C) 2016 Elsevier Ltd. All rights reserved.
Description
Keywords
[No Keyword]
Journal or Series
Tetrahedron-Asymmetry
WoS Q Value
Q2
Scopus Q Value
N/A
Volume
27
Issue
14-15
