HClO4·SiO2-mediated improved isomerization of glycidic esters to α -Hydroxy-β,γ-unsaturated esters: application in the formal synthesis of (R)-Baclofen and β -phenyl GABA analogues

Basak, Ranjan ; Dharuman, Suresh ; Suman Reddy, Y. ; Doddi, Venkata Ramana ; Vankar, Yashwant D. (2012) HClO4·SiO2-mediated improved isomerization of glycidic esters to α -Hydroxy-β,γ-unsaturated esters: application in the formal synthesis of (R)-Baclofen and β -phenyl GABA analogues Chemistry Letters, 41 (3). pp. 325-327. ISSN 0366-7022

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Official URL: https://www.jstage.jst.go.jp/article/cl/41/3/41_3_...

Related URL: http://dx.doi.org/10.1246/cl.2012.325

Abstract

An efficient isomerization of glycidic esters to corresponding allylic alcohols, viz. α-hydroxy-β-unsaturated esters has been brought about using HClO4·SiO2. Five of these allylic alcohols underwent selective SN2' nucleophilic substitution to generate γ-azido-α,β-unsaturated esters which were readily converted to an antispastic drug Baclofen and four other β -phenyl GABA analogues.

Item Type:Article
Source:Copyright of this article belongs to Chemical Society of Japan.
ID Code:93386
Deposited On:16 Jun 2012 09:31
Last Modified:16 Jun 2012 09:31

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