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Synthesis 1997; 1997(4): 475-479
DOI: 10.1055/s-1997-1201
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Enantioselective Approach Towards Potential Substance P Antagonists via Hetero-Ene Reaction of Phenylglycine Derivatives

Sabine Laschat* , Thomas Fox
  • *Organisch-Chemisches Institut der Universität Münster, Corrensstr. 40, D-48149 Münster, Germany, Fax +49(251)8339772
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Publication Date:
31 December 2000 (online)

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Phenylglycine methyl ester 7 can be converted in a four-step sequence to the aldehyde 11. Lewis acid catalyzed hetero-ene reaction of 11 gave a mixture of 3-hydroxy-2-phenylpiperidines 14a,b with high diastereoselectivity. The major diastereomer 14a was further transformed into 4-isopropyl-3-(2-methoxybenzylamino)-2-phenylpiperidine (19), a compound structurally related to a substance P antagonist, in five steps via azide displacement and reductive amination.

amino acid - hetero-ene reaction - piperidine - substance P antagonist