Development of a Catalytic Platform for Nucleophilic Substitution: Cyclopropenone-Catalyzed Chlorodehydration of Alcohols

Development of a Catalytic Platform for Nucleophilic Substitution: Cyclopropenone-Catalyzed Chlorodehydration of Alcohols

Cyclopropenone makes the switch: 2,3‐Bis‐(p‐methoxyphenyl)cyclopropenone is a highly efficient catalyst for the chlorodehydration of 20 diverse alcohol substrates (see scheme; X=Cl). With oxalyl chloride as catalytic activator, this nucleophilic substitution proceeded through cyclopropenium‐activate...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-12, Vol.50 (51), p.12222-12226
Hauptverfasser: Vanos, Christine M., Lambert, Tristan H.
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols
Catalysis
Catalysts
Chlorides
chlorodehydration
cyclopropenones
Inversions
nucleophilic substitution
Platforms
Switches
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Zusammenfassung:Cyclopropenone makes the switch: 2,3‐Bis‐(p‐methoxyphenyl)cyclopropenone is a highly efficient catalyst for the chlorodehydration of 20 diverse alcohol substrates (see scheme; X=Cl). With oxalyl chloride as catalytic activator, this nucleophilic substitution proceeded through cyclopropenium‐activated intermediates and resulted in complete stereochemical inversion in substrates with chiral centers.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201104638