The application of intramolecular radical cyclizations of acylsilanes in the regiospecific formation of cyclic silyl enol ethers

CH Huang, SY Chang, NS Wang…

Index: Chang, Sheng-Yueh; Jiaang, Weir-Torn; Cherng, Chaur-Donp; Tang, Kuo-Hsiang; Huang, Chih-Hao; Tsai, Yeun-Min Journal of Organic Chemistry, 1997 , vol. 62, # 26 p. 9089 - 9098

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Citation Number: 24

Abstract

Acylsilanes with terminal α-stannyl bromide or xanthate functionalities are prepared. α- Stannyl radicals generated from these acylsilanes undergo intramolecular cyclizations to give cyclic silyl enol ethers regiospecifically. The radical processes involve radical cyclization, Brook rearrangement, and β-fragmentation in sequence. A tributylstannyl group serves as the radical leaving group. The newly formed σ-bond and π-bond are located ...