Convenient asymmetric synthesis of ß-substituted a,a-difluoro-ß-amino acids via Reformatsky Reaction between N-sulfinylimines and ethyl bromodifluoroacetate

ORGN 530

Alexander Sorochinsky, Dmitrii O. Berbasov, and Vadim A. Soloshonok. Department of Chemistry and Biochemistry, University of Oklahoma, 620 Parrington Oval, Norman, OK 73019

The enantiopure N-sulfinylimines were found to be efficient as chiral imine equivalents at high temperature Reformatsky additions with BrZnCF2COOEt, affording an efficient approach to the enantiomerically pure a,a-difluoro-b-amino acids. High chemical and stereochemical yields (drs > 9:1, and as high as 99:1), combined with operationally convenient conditions and inexpensive N-p-toluenesulfinimines, render this method practically useful for preparation of the target amino acids.

Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses 11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster Division of Organic Chemistry The 226th ACS National Meeting, New York, NY, September 7-11, 2003