Scalable methodology for the catalytic, asymmetric alpha-bromination of acid chlorides |
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Authors: | Dogo-Isonagie Cajetan Bekele Tefsit France Stefan Wolfer Jamison Weatherwax Anthony Taggi Andrew E Lectka Thomas |
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Institution: | Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA. |
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Abstract: | The optimization of a practical, catalytic, asymmetric process for the alpha-bromination of acid chlorides to produce synthetically versatile, optically active alpha-bromoesters is reported. A range of products is produced in high enantioselectivity and moderate to good chemical yields with retention of both upon scale-up. The reactions herein are catalyzed by cinchona alkaloid derivatives, with the best performance achieved by the use of a proline cinchona alkaloid conjugate designed in a de novo fashion. |
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