Enantioselective synthesis of 2,3-diphenyl-1,4-butanediol via oxidative coupling of phenylacetic acid chiral 1,1 '-bi-2-naphthyl ester using TiCl4/Et3N

Authors
Rao, VD Periasamy, M
Citation
Vd. Rao et M. Periasamy, Enantioselective synthesis of 2,3-diphenyl-1,4-butanediol via oxidative coupling of phenylacetic acid chiral 1,1 '-bi-2-naphthyl ester using TiCl4/Et3N, TETRAHEDR-A, 11(5), 2000, pp. 1151-1155
Citations number
26
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
5
Year of publication
2000
Pages
1151 - 1155
Database
ISI
SICI code
0957-4166(20000324)11:5<1151:ESO2VO>2.0.ZU;2-8
Abstract
Oxidative coupling of phenylacetic acid eater of homochiral 1,1'-bi-2-napht hol 2 was achieved by reaction with TiCl4/Et3N to obtain the corresponding 2,3-diphenylsuccinic acid derivative 3, which on reduction using the NaBH4/ I-2 reagent gives homochiral 2,3-diphenyl-1,4-butanediol. X-Ray structural analysis was carried out for the compounds (R)-(+)-2 and (R,R,R)-(-)3. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.