Jump to main content
Jump to site search


Diastereodivergent Asymmetric Michael-Alkylation Reaction by Chiral N,N’-Dioxide/Metal Complexes

Abstract

A diastereodivergent asymmetric Michael-alkylation reaction between 3-chloro-oxindoles and β,γ-unsaturated-α-ketonesters is realized by using L-RaPr2/Sc(OTf)3 and L-PrPr2/Mg(OTf)2 metal complexes. Both rel-(1R,2S,3R) and rel-(1S,2S,3R) chiral spiro cyclopropane oxindoles are constructed in good yields, diastereoselectivities and ee values. The diastereodivergent control might come from different alkylation pathway after the Michael addition: intramolecular trapping the aza-ortho-xylylene intermediate or direct SN2 substitution.

Back to tab navigation

Supplementary files

Publication details

The article was received on 21 Jun 2017, accepted on 07 Nov 2017 and first published on 08 Nov 2017


Article type: Edge Article
DOI: 10.1039/C7SC02757E
Citation: Chem. Sci., 2017, Accepted Manuscript
  • Open access: Creative Commons BY license
  •   Request permissions

    Diastereodivergent Asymmetric Michael-Alkylation Reaction by Chiral N,N’-Dioxide/Metal Complexes

    Y. Kuang, B. Shen, L. Dai, Q. Yao, X. Liu, L. Lin and X. Feng, Chem. Sci., 2017, Accepted Manuscript , DOI: 10.1039/C7SC02757E

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements