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Title

Enantioselective addition of MeLi to aromatic imines catalyzed by C2-symmetric tertiary diamine

Authors
Cabello, Noemi
Pinchard, Laurent
Caille, Jean-Claude
Published in Tetrahedron. 2005, vol. 61, no. 37, p. 8939-8946
Abstract Enantioselective addition of methyllithium to aromatic imines catalyzed by C2 symmetric tertiary diamines is described. Eleven diamines have been tested, for which dramatic effect of the nitrogen substitution has been observed. Diamines bearing hindered group close to the nitrogen led to racemic product while homologous hindered diamines led to the best results. Enantiomeric excess up to 74% could be achieved. An explanation of the absolute configuration of the product obtained is given considering the mechanism of the reaction.
Keywords AsymmetryDiaminesOrganolithiumIminesCatalysis
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KIZIRIAN, Jean-Claude et al. Enantioselective addition of MeLi to aromatic imines catalyzed by C2-symmetric tertiary diamine. In: Tetrahedron, 2005, vol. 61, n° 37, p. 8939-8946. https://archive-ouverte.unige.ch/unige:8047

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Deposited on : 2010-06-21

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