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Issue 1, 2017
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Formal [3 + 2] cycloaddition of α-unsubstituted isocyanoacetates and methyleneindolinones: enantioselective synthesis of spirooxindoles

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Abstract

The first enantioselective formal [3 + 2] cycloaddition of α-unsubstituted isocyanoacetates with protecting-group-free methyleneindolinones was developed. A variety of optically enriched 3,3′-pyrrolidinyl spirooxindoles were obtained in excellent yields, and diastereo- and enantioselectivities (up to 99% yield, >20 : 1 dr, 99% ee) with low catalyst loading under mild reaction conditions.

Graphical abstract: Formal [3 + 2] cycloaddition of α-unsubstituted isocyanoacetates and methyleneindolinones: enantioselective synthesis of spirooxindoles

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Publication details

The article was received on 17 Sep 2016, accepted on 19 Oct 2016 and first published on 20 Oct 2016


Article type: Research Article
DOI: 10.1039/C6QO00555A
Citation: Org. Chem. Front., 2017,4, 81-85
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    Formal [3 + 2] cycloaddition of α-unsubstituted isocyanoacetates and methyleneindolinones: enantioselective synthesis of spirooxindoles

    X. Peng, Y. A. Ho, Z. Wang, P. Shao, Y. Zhao and Y. He, Org. Chem. Front., 2017, 4, 81
    DOI: 10.1039/C6QO00555A

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