Chemistry: A European Journal 2011-05-23

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

José L García Ruano, Alejandro Parra, Inés Alonso, Santos Fustero, Carlos del Pozo, Yolanda Arroyo, Ascensión Sanz-Tejedor

Index: Chemistry 17(22) , 6142-7, (2011)

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Abstract

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.