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

…, AC Willis, MS Sherburn, MN Paddon-Row

Index: Tripoli, Regis; Cayzer, Tory N.; Willis, Anthony C.; Sherburn, Michael S.; Paddon-Row, Michael N. Organic and Biomolecular Chemistry, 2007 , vol. 5, # 16 p. 2606 - 2616

Full Text: HTML

Citation Number: 9

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 ...