(E)-STEREOSELECTIVE SYNTHESIS OF VINYLGLYCINES FROM (R)-SERINE VIA ORGANOCOPPER-BF3 AND RELATED REAGENTS

Authors
IBUKA T SUZUKI K HABASHITA H OTAKA A TAMAMURA H MIMURA N MIWA Y TAGA T FUJII N
Citation
T. Ibuka et al., (E)-STEREOSELECTIVE SYNTHESIS OF VINYLGLYCINES FROM (R)-SERINE VIA ORGANOCOPPER-BF3 AND RELATED REAGENTS, Journal of the Chemical Society, Chemical Communications, (18), 1994, pp. 2151-2152
Citations number
23
Categorie Soggetti
Chemistry
Journal title
Journal of the Chemical Society, Chemical Communications → ACNP
ISSN journal
00224936
Issue
18
Year of publication
1994
Pages
2151 - 2152
Database
ISI
SICI code
0022-4936(1994):18<2151:(SOVF(>2.0.ZU;2-6
Abstract
The stereoselective synthesis of biologically important vinylglycine d erivatives by reaction of homochiral 4-methoxycarbonyl-5-vinyloxazolid in-2-ones with organocopper reagents is described; 4,5-trans-oxazolidi n-2-one 6 yields (E)-vinylglycines as the major products by treatment with the 'higher order' cyanocuprate-BF3 reagents or trialkylzincates in the presence of cuprous cyanide, 4,5-cis-oxazolidin-2-one 10 afford s only the desired (E)-vinylglycines.