Carbon-carbon bond formation in reactions of PhIO. cntdot. HBF4-silyl enol ether adduct with alkenes or silyl enol ethers

VV Zhdankin, M Mullikin, R Tykwinski…

Index: Zhdankin, Viktor V.; Mullikin, Michelle; Tykwinski, Rik; Berglund, Bruce; Caple, Ronald; et al. Journal of Organic Chemistry, 1989 , vol. 54, # 11 p. 2605 - 2608

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Citation Number: 53

Abstract

A new method for generation of reactive a-ketomethyl aryliodonium intermediates from silyl enol ethers and PhIO-HBF, has been developed. Reactions of PhI0. HBF4/silyl enol ether adduct with alkenes (1-hexene, cyclohexene, a-methylstyrene, allyltrimethylsilane, 2, 3- dimethyl-2-butene) yielded products of allylic alkylation or (in case of 2, 3-dimethyl-2- butene) a substituted dihydrofuran. Reactions of adducts from PhIO/HBF, and silyl enol ...

~91%

~40%

~46%

~41%

~61%

~30%

~33%

~51%

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