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Oxazaphospholidine-oxide as an Efficient ortho-Directing Group for the Diastereoselective Deprotonation of Ferrocene

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posted on 19.01.2006, 00:00 by Daniele Vinci, Nuno Mateus, Xiaofeng Wu, Fred Hancock, Alexander Steiner, Jianliang Xiao
Ortho-lithiation of (2R,4S,5R)-3,4-dimethyl-2-ferrocenyl-5-phenyl[1,3,2]oxazaphospholidine 2-oxide 2 was carried out with diastereoselectivity of >99%, affording a new and efficient way for introducing planar chirality into the ferrocene backbone. Various electrophiles were used to quench the lithiated species, showing the wide applicability of the new ortho-directing group and its potential to generate ligands for use in asymmetric catalysis.