STEREOSPECIFIC INTERNAL ALKYLATION OF TERMINAL GAMMA,DELTA-EPOXY ACRYLATES

Authors
MIYAZAWA M ISHIBASHI N OHNUMA S MIYASHITA M
Citation
M. Miyazawa et al., STEREOSPECIFIC INTERNAL ALKYLATION OF TERMINAL GAMMA,DELTA-EPOXY ACRYLATES, Tetrahedron letters, 38(19), 1997, pp. 3419-3422
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
19
Year of publication
1997
Pages
3419 - 3422
Database
ISI
SICI code
0040-4039(1997)38:19<3419:SIAOTG>2.0.ZU;2-U
Abstract
The alkylation of ethyl (S)- and (R)-4,5-epoxy-2-pentenoates (11) and (12), chiral terminal gamma,delta-epoxy acrylates prepared from D-mann itol, by trialkylaluminum in the presence of water occurs regioselecti vely at the gamma position, i.e., at the internal position, to yield a sole product respectively with net inversion of configuration. The me thod provides useful chiral synthons for natural product synthesis. (C ) 1997 Elsevier Science Ltd.