PREPARATION AND SYNTHETIC UTILITY OF OXASILACYCLOPENTANE ACETALS DERIVED FROM SILIRANES

Authors
SHAW JT WOERPEL KA
Citation
Jt. Shaw et Ka. Woerpel, PREPARATION AND SYNTHETIC UTILITY OF OXASILACYCLOPENTANE ACETALS DERIVED FROM SILIRANES, Tetrahedron, 53(48), 1997, pp. 16597-16606
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
48
Year of publication
1997
Pages
16597 - 16606
Database
ISI
SICI code
0040-4020(1997)53:48<16597:PASUOO>2.0.ZU;2-A
Abstract
The insertion of formamides into a C-Si bond of silirane trans-1 provi des a facile route to the oxasilacyclopentane acetate 5 (86% overall y ield). Stereoselective carbon-carbon bond formation on the derived oxo nium ion was achieved by addition of the silyl enol ether of acetophen one (92:8 selectivity, 79% yield) and 3-pentanone (92:5:3 selectivity, 100% yield). These results demonstrate the potential of siliranes as intermediates in organic synthesis. (C) 1997 Elsevier Science Ltd.