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. 2006 Nov 10;71(23):8946-9.
doi: 10.1021/jo061522l.

Scalable methodology for the catalytic, asymmetric alpha-bromination of acid chlorides

Cajetan Dogo-Isonagie  1 , Tefsit Bekele, Stefan France, Jamison Wolfer, Anthony Weatherwax, Andrew E Taggi, Thomas Lectka
Affiliations

Scalable methodology for the catalytic, asymmetric alpha-bromination of acid chlorides

Cajetan Dogo-Isonagie et al. J Org Chem. .

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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