A mild method for protodesilylation of alpha-dimethylphenylsilyl ester substrates

Authors
Poliskie, GM Mader, MM van Well, R
Citation
Gm. Poliskie et al., A mild method for protodesilylation of alpha-dimethylphenylsilyl ester substrates, TETRAHEDR L, 40(4), 1999, pp. 589-592
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
4
Year of publication
1999
Pages
589 - 592
Database
ISI
SICI code
0040-4039(19990122)40:4<589:AMMFPO>2.0.ZU;2-W
Abstract
Mild conditions (1.2 eq. Hg(OAc)(2), 1.2 eq. TBAF in 1:1 MeOH/THF; 35 min a t 0 degrees C) have been developed for the protodesilylation of alpha-dimet hylphenylsilyl esters. An enolate-dependent mechanism for the reaction was supported through studies indicating the clean incorporation of deuterium. To further investigate the mechanism, the optimal conditions as well as the kinetics of the reaction were explored, (C) 1999 Elsevier Science Ltd. All rights reserved.