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

D J Tantillo; K N Houk; M E Jung

doi:10.1021/jo001172h

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

J Org Chem. 2001 Mar 23;66(6):1938-40. doi: 10.1021/jo001172h.

Authors

D J Tantillo¹, K N Houk, M E Jung

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095-1569, USA.

PMID: 11300884
DOI: 10.1021/jo001172h

Abstract

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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Amides / chemistry*
Esters / chemistry*
Molecular Structure
Stereoisomerism

Substances

Amides
Esters