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  • Title: Convenient asymmetric synthesis of beta-substituted alpha,alpha-difluoro-beta-amino acids via Reformatsky reaction between Davis' N-sulfinylimines and ethyl bromodifluoroacetate.
    Author: Sorochinsky A, Voloshin N, Markovsky A, Belik M, Yasuda N, Uekusa H, Ono T, Berbasov DO, Soloshonok VA.
    Journal: J Org Chem; 2003 Sep 19; 68(19):7448-54. PubMed ID: 12968899.
    Abstract:
    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.
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