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On the Origin of π-Facial Diastereoselectivity in Nucleophilic Additions to Chiral Carbonyl Compounds 3. Rotational Profiles of 2-Methoxypropanal and 2-N,N-Dimethylaminopropanal.

MPS-Authors

Frenking,  G.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Fachbereich Chemie, Philipps-Universität Marburg;

Köhler,  K.F.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Fachbereich Chemie, Philipps-Universität Marburg;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58919

Reetz,  Manfred T.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Fachbereich Chemie, Philipps-Universität Marburg;

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Citation

Frenking, G., Köhler, K., & Reetz, M. T. (1993). On the Origin of π-Facial Diastereoselectivity in Nucleophilic Additions to Chiral Carbonyl Compounds 3. Rotational Profiles of 2-Methoxypropanal and 2-N,N-Dimethylaminopropanal. Tetrahedron, 49(19), 3971-3982. doi:10.1016/S0040-4020(01)89911-7.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0023-CAF7-4
Abstract
The rotational profiles of 2-methoxypropanal and 2-N,N-dimethylaminopropanal are theoretically predicted using ab initio methods at the MP2/6-31G(d)//3-21G level of theory. The conformational energies show a strong dependence on the torsion angle not only around the CπC bond but also around the CπR (R=OMe, NMe2) bond.