Tetrahedron Letters

Silicon-directed beckmann fragmentation. Catalytic cleavage of cyclic β-trimethylsilylketoxime acetates with trimethylsilyl trifluoromethanesulfonate

H Nishiyama, K Sakuta, N Osaka, K Itoh

Index: Nishiyama, Hisao; Sakuta, Koji; Osaka, Noriyuki; Itoh, Kenji Tetrahedron Letters, 1983 , vol. 24, # 37 p. 4021 - 4024

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Citation Number: 19

Abstract

Abstract Cyclic (E)-β-trimethylsilylketoxime acetates were effectively cleaved by a catalytic action of trimethylsilyl trifluoromethanesulfonate to give the corresponding unsaturated nitriles. The fragmentation in the Beckmann rearrangement is completely controlled and directed by trimethylsilyl group to lead regio-and stereospecific formation of the double bond.