1,5-Induction in reactions of 4-alkoxy-2-trimethylsilylalk-2-enyl(tributyl)stannanes with aldehydes

Authors
Taylor, NH Thomas, EJ
Citation
Nh. Taylor et Ej. Thomas, 1,5-Induction in reactions of 4-alkoxy-2-trimethylsilylalk-2-enyl(tributyl)stannanes with aldehydes, TETRAHEDRON, 55(29), 1999, pp. 8757-8768
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
29
Year of publication
1999
Pages
8757 - 8768
Database
ISI
SICI code
0040-4020(19990716)55:29<8757:1IRO4>2.0.ZU;2-C
Abstract
2-Trimethylsilylalk-2-enylstannanes undergo tin(IV) chloride promoted react ions with aldehydes to give homoallylic alcohols with retention of the 2-tr imethylsilyl group. 4-Alkoxy-2-aimethylsilylalk-2-enyl(tributyl)stannane 31 reacts with aldehydes under these conditions with excellent stereoselectiv ity in favour of the 1,5-syn-(E)-products 32 - 35. Preliminary studies into the chemistry of these vinylsilanes have been carried out. (C) 1999 Elsevi er Science Ltd. All rights reserved.