Alkynes Q 0087 DBU-Promoted Facile, Chemoselective Cleavage of Acetylenic TMS Group. -It is disclosed that DBU is highly efficient even in the presence of bulkier alkyl silyl ethers or other base-sensitive groups. -(YEOM, C.-E.; KIM, M. J.; CHOI, W.; KIM*, B. M.; Synlett 2008, 4, 565-568; Dep. Chem., Coll. Nat. Sci., Seoul Natl. Univ., Seoul 151-742, S. Korea; Eng.) -Mais 28-068
Acetylenic trimethylsilyl (TMS) groups were efficiently removed using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). 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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