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Issue 16, 2007
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Stereocontrol of intramolecular Diels–Alder reactions by an allylic diphenylcyclopropyl group

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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

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Supplementary files

Article information


Submitted
01 Jun 2007
Accepted
19 Jun 2007
First published
13 Jul 2007

Org. Biomol. Chem., 2007,5, 2606-2616
Article type
Paper

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

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