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

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.

alkylation - palladium - asymmetric catalysis - hetero­cycle

References and Notes

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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.