FACE SELECTIVITY IN DIELS-ALDER REACTION OF 4-SUBSTITUTED SEMICYCLIC DIENES WITH DIENOPHILES

Authors
NAGASHIMA S TAKAOKA Y KAWAKAMI K SHIRO M KANEMATSU K
Citation
S. Nagashima et al., FACE SELECTIVITY IN DIELS-ALDER REACTION OF 4-SUBSTITUTED SEMICYCLIC DIENES WITH DIENOPHILES, Heterocycles, 40(2), 1995, pp. 507-510
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
40
Issue
2
Year of publication
1995
Pages
507 - 510
Database
ISI
SICI code
0385-5414(1995)40:2<507:FSIDRO>2.0.ZU;2-7
Abstract
Face selectivity in Diels-Alder reactions of the semicyclic dienes (1a ) and (1b) with maleic anhydride (MA) and N-phenylmaleimide (NPM) was examined. Cycloaddition reaction of 1 with MA occurred preferentially from the diene face anti to the allylic hydroxy group, on the other ha nd, the cycloaddition with NPM occurred preferentially from the syn to the hydroxy group.