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.
Thermolysis of the 3,5-hexadienyl acrylates (a) proceeds via the transition state E in which the connecting chain adopts a boatlike conformation due to a preference for maintaining ester overlap to afford the products b with good diastereoselectivity.
Jung
ME
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569.
Huang
A
Johnson
TW