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Paper

Org. Biomol. Chem., 2007, 5, 2606 - 2616, DOI: 10.1039/b708324f

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

Regis Tripoli, Tory N. Cayzer, Anthony C. Willis, Michael S. Sherburn and Michael N. Paddon-Row

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.

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