Premium
Chiral Monofluorobenzyl Carbanions: Synthesis of Enantiopure β‐Fluorinated β‐Phenylethylamines
Author(s) -
García Ruano José L.,
Parra Alejandro,
Alonso Inés,
Fustero Santos,
del Pozo Carlos,
Arroyo Yolanda,
SanzTejedor Ascensión
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100455
Subject(s) - enantiopure drug , carbanion , chemistry , organic chemistry , enantioselective synthesis , catalysis
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 t BuLi, which occurs without epimerization at the benzylic position, provides the quickest entry to enantiomerically pure β‐fluorinated β‐phenylethylamines.