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

研究成果: 雜誌貢獻文章

7 引文 斯高帕斯(Scopus)

摘要

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.

原文英語
頁(從 - 到)3046-3049
頁數4
期刊Organic Letters
18
發行號13
DOIs
出版狀態已發佈 - 2016 七月 1

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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