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  • Title: Asymmetric synthesis of new beta,beta-difluorinated cyclic quaternary alpha-amino acid derivatives.
    Author: Fustero S, Sanchez-Roselló M, Rodrigo V, del Pozo C, Sanz-Cervera JF, Simón A, Ramírez de Arellano C.
    Journal: Org Lett; 2006 Aug 31; 8(18):4129-32. PubMed ID: 16928091.
    Abstract:
    The synthesis of new beta,beta-difluorinated cyclic quaternary alpha-amino acid derivatives 1 in which a ring-closing metathesis reaction (RCM) constitutes the key step is described. The approach employs imidoyl chlorides 3 as fluorinated building blocks, and the overall process involves the stereoselective creation of a quaternary stereocenter. Complete selectivity was achieved when (R)-phenylglycinol methyl ether was used as chiral auxiliary, allowing for the preparation of new six-membered cyclic fluorinated alpha-amino acids as single enantiomers.
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