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DBU-Promoted Facile, Chemoselective Cleavage of Acetylenic TMS Group

Chang-Eun Yeom, Mi Jeong Kim, Whail Choi, B. Moon Kim*

*School of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151747, Korea, Email: kimbmsnu.ac.kr

C.-E. Yeom, M. J. Kim, W. Choi, B. M. Kim, Synlett, 2008, 565-568.

DOI: 10.1055/s-2008-1032078


Abstract

With either 1.0 or even 0.1 equivalents of DBU, smooth desilylation of various terminal acetylenic TMS groups was accomplished selectively in the presence of alkyl silyl ethers and other base-labile groups. Furthermore, more sterically hindered terminal acetylenic silyl groups such as TBDMS and TIPS remained intact under these conditions.

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Key Words

DBU, silylacetylenes, chemoselective, deprotection


ID: J60-Y2008-0610