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Diastereodivergent asymmetric Michael-alkylation reactions using chiral N,N′-dioxide/metal complexes

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Abstract

A diastereodivergent asymmetric Michael-alkylation reaction between 3-chloro-oxindoles and β,γ-unsaturated-α-ketoesters has been achieved using L-RaPr2/Sc(OTf)3 and L-PrPr2/Mg(OTf)2 metal complexes as catalysts. Both rel-(1R,2S,3R) and rel-(1S,2S,3R) chiral spiro cyclopropane oxindoles were constructed in good yields, diastereoselectivities and ee values. The diastereodivergent control may originate from different alkylation pathways after the Michael addition, with either intramolecular trapping of the aza-ortho-xylylene intermediate or direct SN2 substitution.

Graphical abstract: Diastereodivergent asymmetric Michael-alkylation reactions using chiral N,N′-dioxide/metal complexes

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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., 2018, Advance Article
  • Open access: Creative Commons BY license
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    Diastereodivergent asymmetric Michael-alkylation reactions using chiral N,N′-dioxide/metal complexes

    Y. Kuang, B. Shen, L. Dai, Q. Yao, X. Liu, L. Lin and X. Feng, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C7SC02757E

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