Abstract

We report simple and efficient methods for the preparation of enantiomerically pure spiro[benzo[ c]thiophene-1(3 H),4′-piperidine]-(2 S)-oxide ( S)- 1, a key intermediate for the synthesis of tachykinin receptor antagonist, by resolution and asymmetric sulfoxidation. Racemic ( RS)- 1 can be resolved with ( S)-(+)-mandelic acid in acetonitrile to give ( S)- 1 of >99% ee. We also describe the asymmetric sulfoxidation of sulfide 5 in excellent enantiomeric excess and high chemical yield by the use of the Davis reagent.

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