Olefinic stereoselection in the [2,3]-Wittig rearrangement of alpha,beta-disubstituted allylic ethers forming trisubstituted olefins

Authors
Tomooka, K Igarashi, T Kishi, N Nakai, T
Citation
K. Tomooka et al., Olefinic stereoselection in the [2,3]-Wittig rearrangement of alpha,beta-disubstituted allylic ethers forming trisubstituted olefins, TETRAHEDR L, 40(34), 1999, pp. 6257-6260
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
34
Year of publication
1999
Pages
6257 - 6260
Database
ISI
SICI code
0040-4039(19990820)40:34<6257:OSIT[R>2.0.ZU;2-K
Abstract
The E/Z-selectivities in the [2,3]-Wittig rearrangements of secondary beta- (methyl or silyl)allylic ethers are shown to depend critically on the natur e of groups on the carbanion terminus, thereby permitting elucidation of th e structural requirements for attaining high Z-selectivity. (C) 1999 Elsevi er Science Ltd. All rights reserved.