A Mechanistic Study on the Catalytic, Asymmetric α-Bromination of Acid Chlorides

The mechanism of the catalytic, asymmetric α‐bromination of acid chlorides is probed through a series of crossover experiments, ion‐pairing tests, and kinetic resolution studies to shed light on the factors that contribute to, and limit the production of, optically‐active α‐bromo esters. In order to...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2007-03, Vol.2007 (7), p.1091-1100
Main Authors: Dogo-Isonagie, Cajetan, Bekele, Tefsit, France, Stefan, Wolfer, Jamison, Weatherwax, Anthony, Taggi, Andrew E., Paull, Daniel H., Dudding, Travis, Lectka, Thomas
Format: Article
Language:English
Subjects:
Asymmetric
Catalytic
Enantioselective
α-Bromination
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Summary:The mechanism of the catalytic, asymmetric α‐bromination of acid chlorides is probed through a series of crossover experiments, ion‐pairing tests, and kinetic resolution studies to shed light on the factors that contribute to, and limit the production of, optically‐active α‐bromo esters. In order to understand better the observed sense of induction, as well as the high degree of enantiomeric excess exhibited by these products, extensive molecular modeling is employed on the relevant transition states. Finally, the usefulness of the α‐bromo ester products is demonstrated by their simple derivatization into chiral epoxides.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200600819