Dihydrooxazine N-Oxide Intermediates as Resting States in Organocatalytic Kinetic Resolution of Functionalized Nitroallylic Amines with Aldehydes

Ramani Gurubrahamam, Yan Ming Chen, Wan Yun Huang, Yu Te Chan, Hsiang Kai Chang, Ming Kang Tsai, Kwunmin Chen

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Kinetic resolution of nitroallylic amines was established using chiral α,α-l-diphenylprolinol silyl ether auxiliary through isolation of the dihydrooxazine N-oxide intermediates. Further hydrolyzing the resting states provided tetrahydropyridines in high chemical yields and high to excellent stereoselectivities (up to >20:1 dr and 98% ee). A detailed mechanistic explanation for stereoselective protonation in the dihydrooxazine was probed computationally. In addition, the probable intermediates in α-halogenation of aldehydes (masked with enamines) were isolated to provide crystallographic evidence.

Original languageEnglish
Pages (from-to)3046-3049
Number of pages4
JournalOrganic Letters
Volume18
Issue number13
DOIs
Publication statusPublished - 2016 Jul 1

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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