HClO4·SiO2-mediated Improved Isomerization of Glycidic Esters to α-Hydroxy-β,γ-unsaturated Esters: Application in the Formal Synthesis of (<i>R</i>)-Baclofen and β-Phenyl GABA Analogues

• Ranjan Basak

  Department of Chemistry, Indian Institute of Technology

• Suresh Dharuman

  Department of Chemistry, Indian Institute of Technology

• Y Suman Reddy

  Department of Chemistry, Indian Institute of Technology

• Venkata Ramana Doddi

  Department of Chemistry, Indian Institute of Technology

• Yashwant D Vankar

  Department of Chemistry, Indian Institute of Technology

Abstract

An efficient isomerization of glycidic esters to corresponding allylic alcohols, viz. α-hydroxy-β,γ-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.

Journal

• Chemistry Letters

  Chemistry Letters 41 (3), 325-327, 2012-02-25

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360002219111678464
• NII Article ID: 10030224719
• NII Book ID: AA00603318
• DOI: 10.1246/cl.2012.325
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/41/3/325/55638316/cl.2012.325.pdf
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