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
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.
Basak, Ranjan,Dharuman, Suresh,Reddy, Y. Suman,Doddi, Venkata Ramana,Vankar, Yashwant D.
supporting information; experimental part
p. 325 - 327
(2012/06/01)
Nafion-H catalyzed isomerization of glycidic to α-hydroxy-β,γ- unsaturated esters: Application in the synthesis of a trifluoromethylated vinylic epoxide
Facile Nafion-H catalyzed isomerization of glycidic esters to α- hydroxy-β,γ-unsaturated esters is reported. These compounds are useful synthetic intermediates. Application in the synthesis of a trifluoromethylated vinylic epoxide is demonstrated.
Foote, Kevin M.,John, Matthew,Pattenden, Gerald
p. 363 - 365
(2007/10/03)
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