An Intramolecular Organocatalytic Cyclopropanation Reaction

An Intramolecular Organocatalytic Cyclopropanation Reaction

Nucleophilic tertiary amines catalyze an intramolecular cyclopropanation reaction to give [n.1.0]bicycloalkanes in good yield (see scheme). The reaction is tolerant of a wide range of functional groups and is highly diastereoselective. Furthermore, when a catalytic amount of a chiral cinchona alkalo...

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Veröffentlicht in:Angewandte Chemie International Edition 2004-05, Vol.43 (20), p.2681-2684
Hauptverfasser: Bremeyer, Nadine, Smith, Stephen C., Ley, Steven V., Gaunt, Matthew J.
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Cyclization
cyclopropanation
Cyclopropanes - chemistry
diastereoselectivity
enantioselectivity
homogeneous catalysis
Models, Chemical
Molecular Structure
Stereoisomerism
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Zusammenfassung:Nucleophilic tertiary amines catalyze an intramolecular cyclopropanation reaction to give [n.1.0]bicycloalkanes in good yield (see scheme). The reaction is tolerant of a wide range of functional groups and is highly diastereoselective. Furthermore, when a catalytic amount of a chiral cinchona alkaloid derivative is used the reaction produces cyclopropanes with enantiomeric excess of 94 %. EWG=electron withdrawing group.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200454007