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 ...
Related Articles:
[Dembkowski, Leszek; Witt, Dariusz; Rachon, Janusz Phosphorus, Sulfur and Silicon and Related Elements, 1997 , vol. 127, p. 143 - 157]
The absolute configuration of cis-2-phenylcyclopropane-carboxylic acid and related compounds
[Aratani,T. et al. Tetrahedron, 1970 , vol. 26, p. 1675 - 1684]
[Mulzer, Johann; Huisgen, Rolf; Arion, Vladimir; Sustmann, Reiner Helvetica Chimica Acta, 2011 , vol. 94, # 8 p. 1359 - 1388]
Cyclopropanes: The Cyclopropyl Carbanion1, 2
[Walborsky; Hornyak Journal of the American Chemical Society, 1955 , vol. 77, p. 6026,6029]
[Dembkowski, Leszek; Witt, Dariusz; Rachon, Janusz Phosphorus, Sulfur and Silicon and Related Elements, 1997 , vol. 127, p. 143 - 157]