4.6 Article

Chiral Monofluorobenzyl Carbanions: Synthesis of Enantiopure β-Fluorinated β-Phenylethylamines

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 22, Pages 6142-6147

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201100455

Keywords

asymmetric synthesis; fluorinated carbanions; ionic liquids; stereoselectivity; sulfinylimines

Funding

  1. Spanish Government [CTQ2009-12168, CTQ2010-19744]
  2. Comunidad Autonoma de Madrid [AVANCAT S2009/PPQ1634]
  3. Generalitat Valenciana [PROME-TEO2010/061/GV]
  4. Ramon y Cajal

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The preparation of a stabilized monofluorobenzyl carbanion by means of a remote homochiral sulfinyl group and its completely stereoselective reactions with N-p-tolylsulfinylimines are described. The use of these reactions followed by the simultaneous removal of both chiral auxiliaries with tBuLi, which occurs without epimerization at the benzylic position, provides the quickest entry to enantiomerically pure beta-fluorinated beta-phenylethylamines.

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