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

Siang en Syu, Tzu Ting Kao, Wen-Wei Lin

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46 Citations (Scopus)

Abstract

(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.

Original languageEnglish
Pages (from-to)891-897
Number of pages7
JournalTetrahedron
Volume66
Issue number4
DOIs
Publication statusPublished - 2010 Jan 23

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Keywords

  • Ketones
  • Michael addition
  • Nitroolefins
  • Organocatalysis
  • Stereoselectivity

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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