Christophe Grosjean - A (-)-Sparteine-Directed Highly Enantioselective Synthesis of Boroproline. Solid- and Solution-State Structure and Properties

Version 1

      Publication Details (including relevant citation   information):

      Batsanov, A. S.; Grosjean, C.; Schuetz, T.; Whiting, A. J.   Org. Chem., 2007, 72, 6276‐6279


      A two-step, direct asymmetric synthesis of the trifluoroacetate

      ammonium salt of boroproline is reported. (-)-

      Sparteine-mediated lithiation of N-Boc-pyrrolidine afforded

      N-Boc-aminoboronic acid in good yield and enantioselectivity

      as determined by HPLC (pinanediol ester). Deprotection

      using TFA yielded the ammonium salt; full characterization

      data are presented, and the structure in aqueous

      solution and the occurrence of a B-N species are discussed.

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