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Synlett 2011(20): 2939-2942  
DOI: 10.1055/s-0031-1289878
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Chiral Key Intermediate of Neurokinin Antagonist SSR 240600 by Asymmetric Allylic Alkylation

Jérôme Keldenicha,c, Christophe Michona,b,c, Audrey Nowickia,c, Francine Agbossou-Niedercorn*a,b,c
a Université Lille Nord de France, 59000 Lille, France
Fax: +33(3)20436585; e-Mail: francine.agbossou@ensc-lille.fr;
b CNRS, UCCS UMR 8181, 59655 Villeneuve d’Ascq, France
c ENSCL, CCM-CCCF, Bât C7, BP 90108, 59652 Villeneuve d’Ascq, France
Further Information

Publication History

Received 25 August 2011
Publication Date:
11 November 2011 (online)

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Abstract

The preparation of optically active morpholine-2-aryl-2-acetaldehyde from morpholine-2-aryl-3-one is reported. The quaternary carbon is introduced during a palladium-promoted asymmetric allylic alkylation. This is a useful intermediate in the synthesis and development of potent NK antagonist.

Key words

alkylation - palladium - asymmetric catalysis - hetero­cycle

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13

Michon, C.; Béthegnies, A.; Roussel, P.; Capet, F.; de Filippis, A.; Cossy, J.; Agbossou-Niedercorn, F. manuscript in preparation.

17

X-ray crystal data of compound II were deposited under reference CCDC 836129. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre: www.ccdc.cam.ac.uk/data_request/cif.