TiCl14 promoted reaction of aldehydes with 1,5-dienyl allylsilanes: addition accompanied by cyclization

Authors
Vidari, G Bonicelli, MP Anastasia, L Zanoni, G
Citation
G. Vidari et al., TiCl14 promoted reaction of aldehydes with 1,5-dienyl allylsilanes: addition accompanied by cyclization, TETRAHEDR L, 41(18), 2000, pp. 3471-3474
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
18
Year of publication
2000
Pages
3471 - 3474
Database
ISI
SICI code
0040-4039(20000429)41:18<3471:TPROAW>2.0.ZU;2-B
Abstract
TiCl4 readily promotes the addition of 1,5-dienyl allylsilanes to aliphatic aldehydes with concomitant cyclization to afford 1,3-cis-disubstituted met hylenecyclohexanes with remarkable stereoselectivity. The trimethylsilyl gr oup exerts a strong activating and directing influence on the regioselectiv ity and stereoselectivity of this biomimetic cyclization. (C) 2000 Elsevier Science Ltd. All rights reserved.