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

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  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.

  Address (URL): jean%255D%2BNOT%2B%255Batype%253A%2Bad%255D%2BNOT%2B%255Batype%253A%2Bacs-toc%2 5 5D&searchHistoryKey=