Scalable methodology for the catalytic, asymmetric alpha-bromination of acid chlorides.
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.
Dogo-Isonagie
Cajetan
C
Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.
Bekele
Tefsit
T
France
Stefan
S
Wolfer
Jamison
J
Weatherwax
Anthony
A
Taggi
Andrew E
AE
Lectka
Thomas
T
D001966:Bromine / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D004952:Esters; D006843:Hydrocarbons, Chlorinated; D001966:Bromine