Enantioselective organocatalytic Michael Addition of ketones to alkylidene malonates

Siang En Syu, Chan Hui Huang, Ko Wei Chen, Chia Jui Lee, Utpal Das, Yeong Jiunn Jang, Wenwei Lin

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4 Citations (Scopus)

Abstract

Organocatalysts bearing sulfide or sulfone functions () were studied for the direct asymmetric Michael addition of ketones and alkylidene malonates. The organocatalyst (S)-2-((naphthalen-2-ylthio)methyl)pyrrolidine, bearing a pyrrolidine and a sulfide moiety, showed a very high catalytic activity in the absence of additives. The reaction condition is mild, and the Michael adducts were obtained in very good enantioselectivities (up to 96%), diastereoselectivities (up to >95:5), and chemical yields (up to 95%). Chirality 24:600-605, 2012. © 2012 Wiley Periodicals, Inc.

Original languageEnglish
Pages (from-to)600-605
Number of pages6
JournalChirality
Volume24
Issue number8
DOIs
Publication statusPublished - 2012 Aug 1

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Keywords

  • Michael addition
  • alkylidene malonate
  • ketones
  • organocatalysis
  • stereoselectivity

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Cite this

Syu, S. E., Huang, C. H., Chen, K. W., Lee, C. J., Das, U., Jang, Y. J., & Lin, W. (2012). Enantioselective organocatalytic Michael Addition of ketones to alkylidene malonates. Chirality, 24(8), 600-605. https://doi.org/10.1002/chir.22055