An asymmetric synthesis of 3-aryl-1,4-oxazin-2-ones: Synthesis of a key intermediate of an NK1 receptor antagonist

Paul N. Devine, Bruce S. Foster, Edward J.J. Grabowski, Paul J. Reider

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Pyrrolidine derived (S)-lactamide auxiliaries mediate a highly diastereoselective coupling reaction between racemic α-halo acids and N-benzylethanolamine. The adducts are readily cyclized upon treatment with a catalytic amount of TsOH giving the above titled compounds in >90% ee. The 4-fluorophenyl substituted oxazinone thus formed is the key intermediate in the synthesis of a potent NK1 receptor antagonist.

Original languageEnglish (US)
Pages (from-to)119-123
Number of pages5
JournalHeterocycles
Volume58
DOIs
StatePublished - Nov 22 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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