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A new imidazole-containing imidazolidinone catalyst for organocatalyzed asymmetric conjugate addition of nitroalkanes to aldehydes

Hojabri, L ; Sharif University of Technology | 2007

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  1. Type of Document: Article
  2. DOI: 10.1002/adsc.200600316
  3. Publisher: Wiley-VCH Verlag , 2007
  4. Abstract:
  5. Herein we report a new organocatalyst for the asymmetric Michael addition of nitroalkanes to α,β-unsaturated aldehydes. This catalyst incorporates a basic imidazole group in addition to the secondary amine responsible for activation of the α,β-unsaturated carbonyl compounds via iminium ion formation. The new organocatalyst is capable of catalyzing the enantioselective carbon-carbon bond formation with a high degree of enantiocontrol providing products in enantiomeric excesses of up to 92% and yields of up to to 91 %. These results constitute the best results so far reported for organocatalyzed Michael additions of nitroalkanes to α,β-unsaturated aldehydes, and provide proof of principle that organocatalysts incorporating two internal basic moieties may find broad application in organocatalyzed Michael additions. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA
  6. Keywords:
  7. Asymmetric catalysis ; C-C coupling ; Iminium ion activation ; Michael addition ; Organocatalysis ; α,β-unsaturated aldehydes
  8. Source: Advanced Synthesis and Catalysis ; Volume 349, Issue 4-5 , 2007 , Pages 740-748 ; 16154150 (ISSN)
  9. URL: https://onlinelibrary.wiley.com/doi/10.1002/adsc.200600316