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Chemistry. 2011 May 23;17(22):6142-7. doi: 10.1002/chem.201100455. Epub 2011 Apr 13.

Chiral monofluorobenzyl carbanions: synthesis of enantiopure β-fluorinated β-phenylethylamines.

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  • 1Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain.


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 β-fluorinated β-phenylethylamines.

Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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