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On the chemoselectivity and mechanism of desilylation of tert-butyldimethylsilyl ethers with TMSOTf

โœ Scribed by Roger Hunter; Wolfgang Hinz; Philip Richards

Book ID
104261307
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
238 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A modified literature procedure is presented for desilylating primary and secondary tert-butyldimethylsilyl ethers involving TMSOTf followed by breakdown of the b/s-silyloxonium ion in methanol. The chemoselectivity of the process with respect to TBDPS, TIPS, MEM, ester, ketal, acetate, benzoate and NBoc functionalities has been evaluated, and a mechanism involving intermediacy of a transient tert-butyldimethylsilylium ion is proposed.

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