A new type of organocatalyst for highly stereoselective Michael addition of ketones to nitroolefins on water

Siang en Syu, Tzu Ting Kao, Wenwei Lin*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

48 引文 斯高帕斯(Scopus)

摘要

(S)-2-((Naphthalen-2-ylsulfonyl)methyl)pyrrolidine, prepared in three steps from (S)-N-Boc-2-[((4-toluenesulfonyl)oxy)methyl]pyrrolidine in 62% overall yield, was used as a new type of organocatalyst bearing a pyrrolidine and a sulfone moiety. It shows very high catalytic activity toward the direct asymmetric Michael reaction of cyclohexanone and nitroolefins. All the corresponding adducts can be furnished in 90-99% yields and with up to 98% ee and over 99:1 dr on water in the presence of this catalyst (15 mol %) without any additive.

原文英語
頁(從 - 到)891-897
頁數7
期刊Tetrahedron
66
發行號4
DOIs
出版狀態已發佈 - 2010 1月 23

ASJC Scopus subject areas

  • 生物化學
  • 藥物發現
  • 有機化學

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