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Development of a Catalytic Platform for Nucleophilic Substitution: Cyclopropenone‐Catalyzed Chlorodehydration of Alcohols
Author(s) -
Vanos Christine M.,
Lambert Tristan H.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201104638
Subject(s) - nucleophilic substitution , catalysis , chemistry , nucleophile , substitution (logic) , activator (genetics) , combinatorial chemistry , alcohol , nucleophilic addition , medicinal chemistry , organic chemistry , computer science , programming language , biochemistry , gene
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.