Regioselective and stereospecific azidation of 1, 2-and 1, 3-diols by azidotrimethylsilane via a Mitsunobu reaction

…, M Wanunu, HS Byun, R Bittman

Index: He, Linli; Wanunu, Meni; Byun, Hoe-Sup; Bittman, Robert Journal of Organic Chemistry, 1999 , vol. 64, # 16 p. 6049 - 6055

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Citation Number: 35

Abstract

A one-pot regio-and stereospecific azidation reaction of 1, 2-and 1, 3-diols with azidotrimethylsilane (Me3SiN3) via a Mitsunobu reaction has been achieved. With 1, 2-and 1, 3-diols, the reaction of triphenylphosphine, diisopropyl azodicarboxylate, and Me3SiN3 in dichloromethane gave regioselective azidation at C-2 and C-3, respectively, in good yield (74-90% combined yield of 1a+ 1b or of 2a+ 2b). However, application of the same ...