Highly Stereoselective Ring Expansion Reactions Mediated by Attractive Cation–n Interactions

…, B Neuenswander, JL Poutsma, J Aubé

Index: Ribelin, Timothy; Katz, Christopher E.; English, Donna G.; Smith, Sherriel; Manukyan, Anna K.; Day, Victor W.; Neuenswander, Benjamin; Poutsma, Jennifer L.; Aube, Jeffrey Angewandte Chemie - International Edition, 2008 , vol. 47, # 33 p. 6233 - 6235

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Citation Number: 45

Abstract

Most stereoselective reactions are ruled by steric effects. In particular, kinetically controlled asymmetric transformations utilizing chiral reagents, auxiliaries, or catalysts succeed because of energy differences in the transition states that most often arise by the minimization of repulsive, nonbonded interactions. Stereoelectronic considerations, which arise when the alignment of particular orbitals are necessary for a successful reaction, can ...