Intramolecular Diels-Alder reactions of ester-linked 1,3,8-nonatrienes

Tory N. Cayzer, Michael N. Paddon-Row*, Damian Moran, Alan D. Payne, Michael S. Sherburn, Peter Turner

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

Penta-1,3-dienyl acrylates undergo kinetically controlled intramolecular Diels-Alder (IMDA) reactions and DFT calculations (B3LYP/6-31+G(d)) predict stereoselectivities that are in very good agreement with the experimental values. The nature of the diene C1 substituent has virtually no influence upon reactivity or trans/cis-stereoselectivity whereas terminal C9 dienophile substituents have a substantial effect on both the reactivity and stereoselectivity of these IMDA reactions. The TSs highlight contributions from strain in the developing tether-containing ring, and steric and electronic effects between tether and dienophile substituents, thus providing insight into the origins of IMDA reactivity and stereoselectivity.

Original languageEnglish
Pages (from-to)5561-5570
Number of pages10
JournalJournal of Organic Chemistry
Volume70
Issue number14
DOIs
Publication statusPublished - 8 Jul 2005
Externally publishedYes

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