Origins of stereoselectivity in intramolecular Diels-Alder cycloadditions of dienes and dienophiles linked by ester and amide tethers

Authors
Tantillo, DJ Houk, KN Jung, ME
Citation
Dj. Tantillo et al., Origins of stereoselectivity in intramolecular Diels-Alder cycloadditions of dienes and dienophiles linked by ester and amide tethers, J ORG CHEM, 66(6), 2001, pp. 1938-1940
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
6
Year of publication
2001
Pages
1938 - 1940
Database
ISI
SICI code
0022-3263(20010323)66:6<1938:OOSIID>2.0.ZU;2-2
Abstract
B3LYP/6-31+G(d) calculations of structures and relative energies for compet ing transition states for intramolecular Diels-Alder reactions of substitut ed 3,5-hexadienyl acrylates and acrylamides show that boatlike conformation s are sometimes favored in the forming ring that includes the tether.