Stereoselective synthesis of vinyloxirane via sulfonium ylides

Authors
Zhou, YG Li, AH Dai, LX Hou, XL
Citation
Yg. Zhou et al., Stereoselective synthesis of vinyloxirane via sulfonium ylides, ACT CHIM S, 58(4), 2000, pp. 473-480
Citations number
27
Categorie Soggetti
Chemistry
Journal title
ACTA CHIMICA SINICA
ISSN journal
05677351 → ACNP
Volume
58
Issue
4
Year of publication
2000
Pages
473 - 480
Database
ISI
SICI code
0567-7351(2000)58:4<473:SSOVVS>2.0.ZU;2-Q
Abstract
Under the phase - transfer condition (CH3CN/KOH/RT), the reaction of the vi nyl - type sulfonium ylides and aldehydes gives mainly trans - vinyloxirane , while at low temperature in the presence of lithium bromide (LiBr/KHMDS/T HF/ - 95 degrees C) the main product is cis - vinyloxiranes. A possible mec hanism for the tuning of the reaction stereochemistry by simply varing the reaction conditions is proposed.