HIGHLY ASYMMETRIC PUMMERER-TYPE REACTION INDUCED BY ETHOXY VINYL ESTERS

Authors
SHIBATA N MATSUGI M KAWANO N FUKUI S FUJIMORI C GOTANDA K MURATA K KITA Y
Citation
N. Shibata et al., HIGHLY ASYMMETRIC PUMMERER-TYPE REACTION INDUCED BY ETHOXY VINYL ESTERS, Tetrahedron : asymmetry, 8(2), 1997, pp. 303-310
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
2
Year of publication
1997
Pages
303 - 310
Database
ISI
SICI code
0957-4166(1997)8:2<303:HAPRIB>2.0.ZU;2-Z
Abstract
Ethoxy vinyl esters (EVE:2) were efficient reagents for promoting the asymmetric Pummerer reaction with high enantioselectivity and high yie ld in contrast to the generally used acid anhydrides. Increasing the e lectron-donating ability on the R function in EVE 2 tended to increase enantioselectivity. Consequently, effective asymmetric rearrangements were achieved using EVEs 2b,c bearing a methoxybenzoyloxy function. ( C) 1997 Elsevier Science Ltd.