DIELS-ALDER REACTION OF ALPHA-SUBSTITUTED ACRYLATES AND ALPHA-(METHYLENE)LACTONES - CONFORMATION OF DIENOPHILES AND ENDO EXO SELECTIVITY/

Authors
TAKEDA K IMAOKA I YOSHII E
Citation
K. Takeda et al., DIELS-ALDER REACTION OF ALPHA-SUBSTITUTED ACRYLATES AND ALPHA-(METHYLENE)LACTONES - CONFORMATION OF DIENOPHILES AND ENDO EXO SELECTIVITY/, Tetrahedron, 50(37), 1994, pp. 10839-10848
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
37
Year of publication
1994
Pages
10839 - 10848
Database
ISI
SICI code
0040-4020(1994)50:37<10839:DROAAA>2.0.ZU;2-R
Abstract
Diels-Alder reaction of 1,6-bis(trimethylsilyloxy)-2,4-hexadiene with alpha-substituted acrylates and 5 to 7- and 9 to 11-membered alpha-(me thylene)lactones has been carried out to examine correlation of dienop hile structure with endo/exo selectivity. While the conformationally f lexible acrylates produced cycloadducts of endo/exo = 59:41 to 74:26, the 5 to 7-membered lactones with rigid s-cis conjugated system provid ed cycloadducts of endo/exo = 13:87 to 32:68 and the 9 to 11-membered lactones which can take both s-cis and s-trans conformation afforded e ndo/exo ratios of 37:63 to 57:43.