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

Organic and Biomolecular Chemistry, ISSN: 1477-0520, Vol: 5, Issue: 16, Page: 2606-2616
2007
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Article Description

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. © The Royal Society of Chemistry.

Bibliographic Details

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

Royal Society of Chemistry (RSC)

Biochemistry, Genetics and Molecular Biology; Chemistry

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