DIASTEREOFACIAL SELECTIVITY IN DIELS-ALDER CYCLOADDITIONS OF METHYL ACRYLATE TO FACIALLY DIFFERENTIATED UNSYMMETRICAL CYCLOHEXA-1,3-DIENES

Authors
COXON JM FONG ST LUNDIE K MCDONALD DQ STEEL PJ MARCHAND AP ZARAGOZA F ZOPE UR RAJAGOPAL D BOTT SG WATSON WH KASHYAP RP
Citation
Jm. Coxon et al., DIASTEREOFACIAL SELECTIVITY IN DIELS-ALDER CYCLOADDITIONS OF METHYL ACRYLATE TO FACIALLY DIFFERENTIATED UNSYMMETRICAL CYCLOHEXA-1,3-DIENES, Tetrahedron, 50(45), 1994, pp. 13037-13048
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
45
Year of publication
1994
Pages
13037 - 13048
Database
ISI
SICI code
0040-4020(1994)50:45<13037:DSIDCO>2.0.ZU;2-E
Abstract
The Diels-Alder cycloadditions of methyl acrylate to the unsymmetrical 2.1.0(2,11).0(4,9).0(4,14).0(9,13)]pentadecadienes 1b-f proceed with a high degree of pi-facial stereoselectivity but only moderate regiose lectivity. The results of fixed model transition state calculations, p erformed in an effort to establish the factors which control selectivi ty in these cycloadditions, are reported.