STEREOSELECTIVE SYNTHESIS OF OXYGENATED TRISUBSTITUTED OLEFINS USING N-YLIDES [2,3]REARRANGMENT

Authors
HONDA K IGARASHI D ASAMI M INOUE S
Citation
K. Honda et al., STEREOSELECTIVE SYNTHESIS OF OXYGENATED TRISUBSTITUTED OLEFINS USING N-YLIDES [2,3]REARRANGMENT, Synlett, (6), 1998, pp. 685
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
6
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):6<685:SSOOTO>2.0.ZU;2-Q
Abstract
[2,3]Sigmatropic rearrangement of N-(ethoxycarbonyl)-methyl-beta-metha llylammonium ylide with an oxygen functionality at the beta-position o r gamma-position forms trisubstituted trans-olefins with high stereose lectivity. On the other hand, the rearrangement of salts having a tigl yl ester moiety instead of a carbethoxy group affords cis-olefins. The present method was applied to the synthesis of plaunotol.