Biphasic Enantioselective Olefin Epoxidation Using Tropos Dibenzoazepinium Catalysts

Several novel chiral iminium TRISPHAT [tris(tetrachlorobenzenediolato)phosphate(V)] salts combining a diphenylazepinium core, chiral exocyclic appendages, and lipophilic counterions have been prepared and tested in biphasic enantioselective olefin epoxidation conditions. Interestingly, the iminium s...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-07, Vol.70 (15), p.5903-5911
Main Authors: Vachon, Jérôme, Pérollier, Céline, Monchaud, David, Marsol, Claire, Ditrich, Klaus, Lacour, Jérôme
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemical Sciences
Chemistry
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:Several novel chiral iminium TRISPHAT [tris(tetrachlorobenzenediolato)phosphate(V)] salts combining a diphenylazepinium core, chiral exocyclic appendages, and lipophilic counterions have been prepared and tested in biphasic enantioselective olefin epoxidation conditions. Interestingly, the iminium salts derived from commercially available (S)- or (R)-1,2,2-trimethylpropylamine can display efficiency similar to those made from l-acetonamine. Variable-temperature NMR spectroscopy (VT-NMR) and circular dichroism (CD) experiments were performed in search of a correlation between good enantioselectivity in the products and high diastereomeric control of the biphenyl axial chirality of the catalysts.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050629q