TY - JOUR
T1 - Stereocontrol of intramolecular Diels-Alder reactions by an allylic diphenylcyclopropyl group
AU - Tripoli, Regis
AU - Cayzer, Tory N.
AU - Willis, Anthony C.
AU - Sherburn, Michael S.
AU - Paddon-Row, Michael N.
PY - 2007
Y1 - 2007
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=34547563527&partnerID=8YFLogxK
U2 - 10.1039/b708324f
DO - 10.1039/b708324f
M3 - Article
SN - 1477-0520
VL - 5
SP - 2606
EP - 2616
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 16
ER -