Synthesis of substituted chiral chromans via organocatalytic kinetic resolution of racemic 3-nitro-2-aryl-2H-chromenes with ketones catalyzed by pyrrolidinyl-camphor-derived organocatalysts

Dhananjay R. Magar, Kwunmin Chen

研究成果: 雜誌貢獻文章

15 引文 斯高帕斯(Scopus)

摘要

Efficient kinetic resolution of racemic 2-aryl-3-nitro-2H-chromenes (1a-l) has been explored with the pyrrolidinyl-camphor derivative 2b as a bifunctional organocatalyst under neat conditions in the presence of AcOH at 0 °C. In general, the organocatalytic asymmetric Michael addition of ketones proceeded smoothly to give the functionalized Michael adducts (3a-n) with good-to-high diastereo- and enantioselectivities (up to 92:8 dr, 93% ee, and 47% yield). The less reactive chromenes (S)-1a-h, k, l and (R)-1i-j were recovered in high chemical yields and moderate optical purity (up to 42% chemical yield and 72% ee).

原文英語
頁(從 - 到)5810-5816
頁數7
期刊Tetrahedron
68
發行號29
DOIs
出版狀態已發佈 - 2012 七月 22

    指紋

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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