Heterocycles

An Asymmetric Synthesis of 3-aryl-1, 4-oxazin-2-ones: Synthesis of a Key Intermediate of an NK1 Receptor Antagonist

PN Devine, BS Foster, EJJ Grabowski, PJ Reider

文献索引：Devine, Paul N.; Foster, Bruce S.; Grabowski, Edward J. J.; Reider, Paul J. Heterocycles, 2002 , vol. 58, p. 119 - 123

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被引用次数: 12

摘要

Résumé/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 NK 1 ...