Tetrahedron

A torquoselective extrusion of isoxazoline N-oxides. Application to the synthesis of aryl vinyl and divinyl ketones for Nazarov cyclization

DP Canterbury, IR Herrick, J Um, KN Houk, AJ Frontier

Index: Canterbury, Daniel P.; Herrick, Ildiko R.; Um, Joann; Houk; Frontier, Alison J. Tetrahedron, 2009 , vol. 65, # 16 p. 3165 - 3179

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Citation Number: 20

Abstract

A mild, convenient reaction sequence for the synthesis of Nazarov cyclization substrates is described. The [3+ 2] dipolar cycloaddition of a nitrone and an electron-deficient alkyne gives an isolable isoxazoline intermediate, which upon oxidation undergoes stereoselective extrusion of nitrosomethane to give aryl vinyl or divinyl ketones.