THE FIRST EXAMPLE OF ENANTIOSELECTIVE CARBENOID ADDITION TO ORGANOCHALCOGEN ATOMS - APPLICATION TO [2,3]SIGMATROPIC REARRANGEMENT OF ALLYLIC CHALCOGEN YLIDES

Authors
NISHIBAYASHI Y OHE K UEMURA S
Citation
Y. Nishibayashi et al., THE FIRST EXAMPLE OF ENANTIOSELECTIVE CARBENOID ADDITION TO ORGANOCHALCOGEN ATOMS - APPLICATION TO [2,3]SIGMATROPIC REARRANGEMENT OF ALLYLIC CHALCOGEN YLIDES, Journal of the Chemical Society, Chemical Communications, (12), 1995, pp. 1245-1246
Citations number
24
Categorie Soggetti
Chemistry
Journal title
Journal of the Chemical Society, Chemical Communications → ACNP
ISSN journal
00224936
Issue
12
Year of publication
1995
Pages
1245 - 1246
Database
ISI
SICI code
0022-4936(1995):12<1245:TFEOEC>2.0.ZU;2-O
Abstract
In the presence of a catalytic amount of chiral copper(i) or rhodium(i i) compounds the enantioselective addition of a carbenoid, derived fro m ethyl diazoacetate, to chalcogen atoms of aryl cinnamyl chalcogenide s affords a diastereoisomeric mixture of ethyl 2-arylchalcogeno-3-phen ylpent-4-enoates via [2,3]sigmatropic rearrangement of the intermediat e chalcogen ylide with up to 41% ee.