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

Research output: Contribution to journalArticle

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

Fingerprint

Malonates
Bearings (structural)
Sulfides
Ketones
Sulfones
Chirality
Enantioselectivity
Catalyst activity
pyrrolidine

Keywords

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

ASJC Scopus subject areas

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

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

Enantioselective organocatalytic Michael Addition of ketones to alkylidene malonates. / Syu, Siang En; Huang, Chan Hui; Chen, Ko Wei; Lee, Chia Jui; Das, Utpal; Jang, Yeong Jiunn; Lin, Wenwei.

In: Chirality, Vol. 24, No. 8, 08.2012, p. 600-605.

Research output: Contribution to journalArticle

Syu, SE, Huang, CH, Chen, KW, Lee, CJ, Das, U, Jang, YJ & Lin, W 2012, 'Enantioselective organocatalytic Michael Addition of ketones to alkylidene malonates', Chirality, vol. 24, no. 8, pp. 600-605. https://doi.org/10.1002/chir.22055
Syu SE, Huang CH, Chen KW, Lee CJ, Das U, Jang YJ et al. Enantioselective organocatalytic Michael Addition of ketones to alkylidene malonates. Chirality. 2012 Aug;24(8):600-605. https://doi.org/10.1002/chir.22055
Syu, Siang En ; Huang, Chan Hui ; Chen, Ko Wei ; Lee, Chia Jui ; Das, Utpal ; Jang, Yeong Jiunn ; Lin, Wenwei. / Enantioselective organocatalytic Michael Addition of ketones to alkylidene malonates. In: Chirality. 2012 ; Vol. 24, No. 8. pp. 600-605.
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