First asymmetric intermolecular bromoesterification catalyzed by chiral Brønsted acid

The first successful enantioselective intermolecular bromoesterification was realized by using a chiral phosphoric acid as a catalyst. The reaction was optimized after screening 2-aminopyridine based basic catalysts, cinchona alkaloid based basic catalysts, and binol backbone based Brønsted acid cat...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 23; no. 3-4; pp. 245 - 251
Main Authors Li, Guang-xun, Fu, Qing-quan, Zhang, Xiao-mei, Jiang, Jun, Tang, Zhuo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.02.2012
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
BROMOLACTONIZATION
HALOCYCLIZATION
DESIGN
MOLECULAR RECOGNITION
COMPLEXES
OLEFINS
ENANTIOSELECTIVE IODOLACTONIZATION
DERIVATIVES
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Summary:The first successful enantioselective intermolecular bromoesterification was realized by using a chiral phosphoric acid as a catalyst. The reaction was optimized after screening 2-aminopyridine based basic catalysts, cinchona alkaloid based basic catalysts, and binol backbone based Brønsted acid catalysts. Up to 70% ee and a moderate yield were achieved under the optimized condition. An ion-pair mechanism has been suggested in order to explain the reaction results.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2012.02.016