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

Gaining control: An attractive electrostatic force stabilizes the conformation of an intermediate (see scheme; n=nonbonded electron), thus controlling the leaving group configuration to give superior diastereoselectivity in an asymmetric ring expansion.

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-08, Vol.47 (33), p.6233-6235
Main Authors: Ribelin, Timothy, Katz, Christopher E, English, Donna G, Smith, Sherriel, Manukyan, Anna K, Day, Victor W, Neuenswander, Benjamin, Poutsma, Jennifer L, Aubé, Jeffrey
Format: Article
Language:English
Subjects:
azides
Azides - chemistry
Cations
electrostatic interations
nonbonded interactions
ring expansion
Schmidt reaction
Stereoisomerism
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Description
Summary:Gaining control: An attractive electrostatic force stabilizes the conformation of an intermediate (see scheme; n=nonbonded electron), thus controlling the leaving group configuration to give superior diastereoselectivity in an asymmetric ring expansion.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200801591