Synthesis of benzylcyanoborane adducts of amines and separation of their enantiomers; SN2 substitution at boron atom

Laurent Charoy; Alain Valleix; Loïc Toupet; Thierry Le Gall; Paul Pham van Chuong; Charles Mioskowski

doi:10.1039/B006265K

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Synthesis of benzylcyanoborane adducts of amines and separation of their enantiomers; S_N2 substitution at boron atomExperimental procedures and characterization data for compounds 5, 6, 7, 8a–c as well as HPLC profiles are available as supplementary data. For direct electronic access see http://www.rsc.org/suppdata/cc/b0/b006265k/

Laurent Charoy,^a Alain Valleix,^a Loïc Toupet,^b Thierry Le Gall,^a Paul Pham van Chuong^a and Charles Mioskowski*^a

Author affiliations

* Corresponding authors

^a CEA-Saclay, Service des Molécules Marquées, Bât. 547, Département de Biologie Cellulaire et Moléculaire, Gif-sur-Yvette cedex, France.
E-mail: charles.mioskowski@cea.fr

^b Université de Rennes 1, Groupe Matière Condensé et Materiaux, UMR 6626, Bât 11A, Campus de Beaulieu, Rennes cedex, France

Abstract

Benzylcyanoborane adducts of several amines were prepared in four steps from toluene, their enantiomers were separated using chiral phase HPLC and an S_N2 pathway was evidenced in the reaction of a trimethylamine-derived enantiomer with pyridine.

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Article information

DOI: https://doi.org/10.1039/B006265K
Article type: Communication
Submitted: 02 Aug 2000
Accepted: 02 Oct 2000
First published: 07 Nov 2000

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Chem. Commun., 2000, 2275-2276

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Synthesis of benzylcyanoborane adducts of amines and separation of their enantiomers; S_N2 substitution at boron atom

L. Charoy, A. Valleix, L. Toupet, T. Le Gall, P. Pham van Chuong and C. Mioskowski, Chem. Commun., 2000, 2275 DOI: 10.1039/B006265K

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