The First Radical Method for the Introduction of an Ethynyl Group Using a Silicon Tether and Its Application to the Synthesis of 2'-Deoxy-2'-C-ethynylnucleosides1

M Sukeda, S Ichikawa, A Matsuda…

Index: Sukeda, Makoto; Ichikawa, Satoshi; Matsuda, Akira; Shuto, Satoshi Journal of Organic Chemistry, 2003 , vol. 68, # 9 p. 3465 - 3475

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Citation Number: 38

Abstract

A novel radical method for the stereoselective introduction of an ethynyl group has been developed. When a solution of ethynyldimethylsilyl (EDMS) or [2-(trimethylsilyl) ethynyl] dimethylsilyl (TEDMS) ethers of trans-2-iodoindanol was treated with Et3B followed by tetrabutylammonium fluoride in toluene, atom transfer 5-exo-cyclization and subsequent elimination occurred to give cis-2-ethynylindanol in high yield. The method was shown to ...