Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 22, Pages 6142-6147Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201100455
Keywords
asymmetric synthesis; fluorinated carbanions; ionic liquids; stereoselectivity; sulfinylimines
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Funding
- Spanish Government [CTQ2009-12168, CTQ2010-19744]
- Comunidad Autonoma de Madrid [AVANCAT S2009/PPQ1634]
- Generalitat Valenciana [PROME-TEO2010/061/GV]
- 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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