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

Tripoli, Regis; Cayzer, Tory; Willis, Anthony; Paddon-Row, Michael; Sherburn, Michael


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...[Show more]

CollectionsANU Research Publications
Date published: 2007
Type: Journal article
Source: Organic and Biomolecular Chemistry
DOI: 10.1039/b708324f


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