The effect of high pressure on the diastereoselectivity of intermolecular all-carbon Diels-Alder reactions

Authors
Tietze, LF Henrich, M Niklaus, A Buback, M
Citation
Lf. Tietze et al., The effect of high pressure on the diastereoselectivity of intermolecular all-carbon Diels-Alder reactions, CHEM-EUR J, 5(1), 1999, pp. 297-304
Citations number
40
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY-A EUROPEAN JOURNAL
ISSN journal
09476539 → ACNP
Volume
5
Issue
1
Year of publication
1999
Pages
297 - 304
Database
ISI
SICI code
0947-6539(199901)5:1<297:TEOHPO>2.0.ZU;2-O
Abstract
The influence of high pressure on the diastereoselectivity of the intermole cular all-carbon Diels - Alder reaction of the phenylbutadienes 1a-c with t he dicyanoethylenes 2a-d to give the cyclohexenes 3-8 is described. The dif ferences in activation volume, aav, for the two pathways leading to cis and trans diastereomers range from - (0.7 +/- 0.8) to - (6.4 +/- 0.6) cm(3) mo l(-1), indicating a pressure-induced increase of diastereoselectivity in fa vour of the cis adducts 3a-d, 5a-d and 7b-d.