Convenient asymmetric synthesis of beta-substituted alpha,alpha-difluoro-beta-amino acids via Reformatsky reaction between Davis' N-sulfinylimines and ethyl bromodifluoroacetate.
The enantiopure Davis' N-sulfinylimines were found to be efficient as chiral imine equivalents in the high-temperature Reformatsky-type additions with BrZnCF(2)COOEt affording an efficient approach to the enantiomerically pure alpha,alpha-difluoro-beta-amino acids. High chemical and stereochemical yields (drs > 9:1, and as high as 99:1) render this method immediately useful for preparing the target amino acids.
Sorochinsky
Alexander
A
Institute of Bioorganic Chemistry and Petrochemistry, Ukrainian Academy of Sciences, Kiev-94, 253660, Ukraine. sorochinsky@bpci.kiev.ua
Voloshin
Natalia
N
Markovsky
Andrey
A
Belik
Michael
M
Yasuda
Nobuhiro
N
Uekusa
Hidehiro
H
Ono
Taizo
T
Berbasov
Dmitrii O
DO
Soloshonok
Vadim A
VA
D000596:Amino Acids / Q000138:chemical synthesis*; D005461:Fluorine / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry
D000596:Amino Acids; D007097:Imines; D013452:Sulfonium Compounds; D005461:Fluorine