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Diastereo- and enantioselective construction of spirooxindole scaffolds through a catalytic asymmetric [3 + 3] cycloaddition

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Abstract

A chiral phosphoric acid-catalyzed asymmetric [3 + 3] cycloaddition of C3-substituted 2-indolylmethanols with isatin-derived azomethine ylides has been established, which afforded chiral spirooxindoles in considerable yields, moderate to good enantioselectivities and excellent diastereoselectivities (up to 85% yield, 96 : 4 er, all >95 : 5 dr).

Graphical abstract: Diastereo- and enantioselective construction of spirooxindole scaffolds through a catalytic asymmetric [3 + 3] cycloaddition

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Publication details

The article was received on 02 May 2017, accepted on 16 May 2017 and first published on 16 May 2017


Article type: Communication
DOI: 10.1039/C7OB01059A
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Diastereo- and enantioselective construction of spirooxindole scaffolds through a catalytic asymmetric [3 + 3] cycloaddition

    C. Li, H. Lu, X. Sun, G. Mei and F. Shi, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01059A

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