Jump to main content
Jump to site search

Issue 16, 2007
Previous Article Next Article

Stereocontrol of intramolecular Diels–Alder reactions by an allylic diphenylcyclopropyl group

Author affiliations

Abstract

Intramolecular Diels–Alder reactions of ester-linked 1,3,8-nonatrienes carrying a diphenylcyclopropyl substituent attached to C1 proceed with high levels of stereoselectivity. The stereochemical outcomes of these reactions are explained by reference to B3LYP/6-31G(d) transition structures. Experimentally, the diphenylcyclopropane rings remain intact through these IMDA reactions, notwithstanding their predicted extremely high degree of asynchronicity (the B3LYP-computed lengths in the IMDA transition structures differ by as much as 1.1 Å), providing support to the notion that these reactions are concerted processes.

Graphical abstract: Stereocontrol of intramolecular Diels–Alder reactions by an allylic diphenylcyclopropyl group

Back to tab navigation

Supplementary files

Publication details

The article was received on 01 Jun 2007, accepted on 19 Jun 2007 and first published on 13 Jul 2007


Article type: Paper
DOI: 10.1039/B708324F
Citation: Org. Biomol. Chem., 2007,5, 2606-2616

  •   Request permissions

    Stereocontrol of intramolecular Diels–Alder reactions by an allylic diphenylcyclopropyl group

    R. Tripoli, T. N. Cayzer, A. C. Willis, M. S. Sherburn and M. N. Paddon-Row, Org. Biomol. Chem., 2007, 5, 2606
    DOI: 10.1039/B708324F

Search articles by author

Spotlight

Advertisements