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

Authors
Hunter, R Hinz, W Richards, P
Citation
R. Hunter et al., On the chemoselectivity and mechanism of desilylation of tert-butyldimethylsilyl ethers with TMSOTf, TETRAHEDR L, 40(18), 1999, pp. 3643-3646
Citations number
27
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
18
Year of publication
1999
Pages
3643 - 3646
Database
ISI
SICI code
0040-4039(19990430)40:18<3643:OTCAMO>2.0.ZU;2-6
Abstract
A modified literature procedure is presented for desilylating primary and s econdary tert-butyldimethylsilyl ethers involving TMSOTf followed by breakd own of the bis-silyloxonium ion in methanol. The chemoselectivity of the pr ocess with respect to TBDPS, TIPS, MEM, ester, ketal, acetate, benzoate and NBoc functionalities has been evaluated, and a mechanism involving interme diacy of a transient tert-butyldimethylsilylium ion is proposed. (C) 1999 E lsevier Science Ltd. All rights reserved.