Please use this identifier to cite or link to this item:
Title: Effect of substituents on enantioselectivity in chiral oxazaborolidine mediated asymmetric ketone reduction reaction
Authors: Balakrishnan, U
Ananthi, N
Velmathi, S
Keywords: L-Valine
Prochiral ketone reduction
Chiral amines
Asymmetric synthesis
Issue Date: Sep-2011
Publisher: NISCAIR-CSIR, India
Abstract: Various new chiral ligands have been synthesized by the condensation of different esters of l-Valine with different substituted salicylaldehydes in order to find the most effective catalyst for the enantioselctive ketone reduction. Chiral amine synthesized from l-Valine methyl ester and 5-chloro salicylaldehyde is found to catalyse the enantioselective reduction of prochiral ketone with high yield (99%) and enantiomeric excess (91%) with 20 mol% of the catalyst using borane dimethylsulphide as a stoichiometric reducutant. Different subsituted prochiral ketones have also been reduced in high yield upto 90% and the corresponding secondary alcohols are formed with good enantiomeric excess upto 99%. The mechanism of this reduction can be very well explained by considering a plausible mechanism for the CBS catalyst.
Description: 1157-1164
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.50B(09) [September 2011]

Files in This Item:
File Description SizeFormat 
IJCB 50B(9) 1157-1164.pdf105.58 kBAdobe PDFView/Open

Items in NOPR are protected by copyright, with all rights reserved, unless otherwise indicated.