ENANTIOSELECTIVE REDUCTION OF KETONES CATALYZED BY 1,3,2-OXAZABOROLIDINES PREPARED FROM PHENYLGLYCINE

Authors
BERENGUER R GARCIA J VILARRASA J
Citation
R. Berenguer et al., ENANTIOSELECTIVE REDUCTION OF KETONES CATALYZED BY 1,3,2-OXAZABOROLIDINES PREPARED FROM PHENYLGLYCINE, Tetrahedron : asymmetry, 5(2), 1994, pp. 165-168
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
2
Year of publication
1994
Pages
165 - 168
Database
ISI
SICI code
0957-4166(1994)5:2<165:EROKCB>2.0.ZU;2-3
Abstract
(R)-B-methyl-4,5,5-triphenyl-1,3,2-oxazaborolidine (1) and (R)-B-allyl -4,5,5-triphenyl-1,3,2-oxazaborolidine (2), prepared from (R)-phenylgl ycine, catalyse the reduction of prochiral ketones with borane, to aff ord the corresponding secondary alcohols in good chemical yields and w ith moderate to high (61%-96%) enantiomeric excesses. These compounds gave the best results reported so far regarding the reduction of linea r alkyl methyl ketones catalysed by oxazaborolidines.