A HIGHLY STEREOSELECTIVE SYNTHESIS OF Z-DISUBSTITUTED OLEFIN BY O-ASSISTED STILL-WITTIG REARRANGEMENT

Authors
FUJII K HARA O FUJITA Y SAKAGAMI Y
Citation
K. Fujii et al., A HIGHLY STEREOSELECTIVE SYNTHESIS OF Z-DISUBSTITUTED OLEFIN BY O-ASSISTED STILL-WITTIG REARRANGEMENT, Tetrahedron letters, 37(3), 1996, pp. 389-392
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
3
Year of publication
1996
Pages
389 - 392
Database
ISI
SICI code
0040-4039(1996)37:3<389:AHSSOZ>2.0.ZU;2-Q
Abstract
In the Still-Wittig rearrangement, stannylated methyl (E)-allylic ethe rs having an aliphatic side chain (la-c) exhibited the usual similar s tereoselectivity, although the poor stereoselectivity was remarkably i mproved by the assistance of an alkoxy moiety on the alkenyl chain. A stannylated methyl (Z)-allylic ether bearing an alkoxy moiety on the a lkenyl chain (le) also showed a high E selectivity as previously repor ted.