A chiral bimetallic Lewis acid as a reaction template. Asymmetric reduction of unsymmetric ketones with LiBH4

Citation
K. Nozaki et al., A chiral bimetallic Lewis acid as a reaction template. Asymmetric reduction of unsymmetric ketones with LiBH4, B CHEM S J, 72(5), 1999, pp. 1109-1113
Citations number
25
Categorie Soggetti
Chemistry
Journal title
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
ISSN journal
00092673 → ACNP
Volume
72
Issue
5
Year of publication
1999
Pages
1109 - 1113
Database
ISI
SICI code
0009-2673(199905)72:5<1109:ACBLAA>2.0.ZU;2-N
Abstract
A new series of chiral bimetallic Lewis acids, 5,5'-bis[(R)-2-aryl-1,3,2-di oxaborolan-4-one], have been prepared from L-(+)-tartaric acid and arylboro nic acids. In the presence of these Lewis acids, unsymmetric ketones were r educed quantitatively by LiBH4, in moderate to good ee's (up to 99% ee). Th e counter cation of BH4- significantly affects the ee's of the products. Th e reaction is applicable to aryl alkyl ketones, dialkyl ketones, and diaryl ketones.