Unusual diastereoselectivity in intramolecular Diels-Alder reactions of substituted 3,5-hexadienyl acrylates. Preference for a boatlike structure of the six-atom tether due to ester overlap

Authors
Jung, ME Huang, A Johnson, TW
Citation
Me. Jung et al., Unusual diastereoselectivity in intramolecular Diels-Alder reactions of substituted 3,5-hexadienyl acrylates. Preference for a boatlike structure of the six-atom tether due to ester overlap, ORG LETT, 2(13), 2000, pp. 1835-1837
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
13
Year of publication
2000
Pages
1835 - 1837
Database
ISI
SICI code
1523-7060(20000629)2:13<1835:UDIIDR>2.0.ZU;2-W
Abstract
Thermolysis of the 3,5-hexadienyl acrylates (a) proceeds via the transition state E in which the connecting chain adopts a boatlike conformation due t o a preference for maintaining ester overlap to afford the products b with good diastereoselectivity.