Free Access
J. Chim. Phys.
Volume 95, Number 2, February 1998
Page(s) 401 - 405
DOI: 10.1051/jcp:1998151

J. Chim. Phys. Vol. 95, N°2  p. 401-405

Multinuclear NMR characterisation of the complexes between chiral 3-aminopyrrolidine lithium amides and n-butyllithium

Y. Prigent, A. Corruble, J.-Y. Valnot, J. Maddaluno, P. Duhamel and D. Davoust

UPRES A 6014 du CNRS, IRCOF, Université de Rouen, 76821 Mont-Saint-Aignan cedex, France

From a set of one- and two-dimensional 1H, 13C and 6Li NMR experiments, we propose the formation of a well organised 1:1 tight complex between substituted 3-aminopyrrolidine lithium amides and n-butyllithium. This complex is probably at the origin of the stereoselection observed in the asymmetric condensation of n-butyllithium onto aromatic aldehydes.

L'étude du transfert de chiralité, dans la réaction de condensation du n-butyllithium sur les aldéhydes aromatiques en présence d'amidures de lithium dérivés d'une série de 3-aminopyrrolidines optiquement actives, est abordée via la détermination de la structure du complexe formé entre amidure et n-BuLi par RMN haut champ 1H, 13C et 6Li dans des conditions proches de celles de la réaction.

Key words: 6Li -- 13C -- 1H NMR -- chiral lithium amide -- 3-aminopyrrolidine -- structure -- lithium amide-alkyllithium complexes

© EDP Sciences 1998

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