Tetrahedron Letters

AuCl 3/AgSbF 6-catalyzed rapid epoxide to carbonyl rearrangement

V Gudla, R Balamurugan

Index: Gudla, Vanajakshi; Balamurugan, Rengarajan Tetrahedron Letters, 2012 , vol. 53, # 39 p. 5243 - 5247

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Citation Number: 20

Abstract

An efficient epoxide to carbonyl rearrangement using catalytic AuCl3/AgSbF6 has been presented. The reactions are fast and high yielding. β-Hydrogen migration takes place exclusively when hydrogen and methyl or substituted methyl groups are present at β-carbon of epoxide. When phenyl/acetyl/benzoyl and hydrogen are available at same carbon atom, migration of the former is preferred over the latter.