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Chiral squaramide-catalysed enantioselective Michael/cyclization cascade reaction of 3-hydroxyoxindoles with α,β-unsaturated N-acylated succinimides

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Abstract

A bifunctional squaramide-catalysed asymmetric Michael/cyclization cascade reaction of 3-hydroxyoxindoles with α,β-unsaturated N-acylated succinimides is disclosed. With quinine-derived squaramide as the catalyst, a broad range of the desired spirooxindole lactone derivatives bearing two contiguous stereocenters were obtained in good yields (up to 89%) with high diastereoselectivities (up to >95 : 5 dr) and excellent enantioselectivities (up to 99% ee).

Graphical abstract: Chiral squaramide-catalysed enantioselective Michael/cyclization cascade reaction of 3-hydroxyoxindoles with α,β-unsaturated N-acylated succinimides

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Publication details

The article was received on 29 May 2017, accepted on 01 Jul 2017 and first published on 03 Jul 2017


Article type: Paper
DOI: 10.1039/C7OB01307H
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Chiral squaramide-catalysed enantioselective Michael/cyclization cascade reaction of 3-hydroxyoxindoles with α,β-unsaturated N-acylated succinimides

    S. Ming, B. Zhao and D. Du, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01307H

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