Diastereospecific synthesis of beta-heterosubstituted alcohols from 1,2-diols via 1,3,2 lambda(5)-dioxaphospholanes

Authors
Cristau, HJ Carteron, M Fruchier, A Pirat, JL
Citation
Hj. Cristau et al., Diastereospecific synthesis of beta-heterosubstituted alcohols from 1,2-diols via 1,3,2 lambda(5)-dioxaphospholanes, CR AC S IIC, 4(8-9), 2001, pp. 711-715
Citations number
10
Categorie Soggetti
Chemistry
Journal title
COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II FASCICULE C-CHIMIE
ISSN journal
13871609 → ACNP
Volume
4
Issue
8-9
Year of publication
2001
Pages
711 - 715
Database
ISI
SICI code
1387-1609(200108/09)4:8-9<711:DSOBAF>2.0.ZU;2-V
Abstract
The stereochemistry of the ring opening of (R,S) or (RR)-4,5-dimethyl-2,2,2 -triphenyl-1,3,2 lambda (5)-dioxaphospholanes (prepared by reaction of (RS) or (R,R)-butane-2,3-diol with dibromotriphenylphosphorane) by aniline or t hiophenol was investigated. The reaction affords stercoselectively the corr esponding beta -anilino- or beta -phenylthioalcohols with a nearly complete inversion of stereochemistry at the stereogenic reaction centre. (C) 2001 Academie des sciences / Editions scientifiques et medicales Elsevier SAS.