Origins of stereoselectivity in intramolecular Diels-Alder cycloadditions of dienes and dienophiles linked by ester and amide tethers.
B3LYP/6-31+G(d) calculations of structures and relative energies for competing transition states for intramolecular Diels-Alder reactions of substituted 3,5-hexadienyl acrylates and acrylamides show that boatlike conformations are sometimes favored in the forming ring that includes the tether.
Tantillo
D J
DJ
Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095-1569, USA.
Houk
K N
KN
Jung
M E
ME
D000577:Amides / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000577:Amides; D004952:Esters