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

Full Text: HTML

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 ...

Related Articles:

Efficient and practical protocol for silylation of hydroxyl groups using reusable lithium perchlorate dispread in silica gel under neutral condition

[Azizi, Najmedin; Yousefi, Rozbeh; Saidi, Mohammad R. Journal of Organometallic Chemistry, 2006 , vol. 691, # 5 p. 817 - 820]

Palladium-catalyzed silylation of alcohols with hexamethyldisilane

[Shirakawa, Eiji; Hironaka, Koji; Otsuka, Hidehito; Hayashi, Tamio Chemical Communications, 2006 , # 37 p. 3927 - 3929]

A novel, chemoselective and efficient microwave-assisted deprotection of silyl ethers with selectfluor

[Saxena, Ira; Deka, Nabajyoti; Sarma, Jadab C.; Tsuboi, Sadao Synthetic Communications, 2003 , vol. 33, # 23 p. 4005 - 4011]

More Articles...