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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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Article information


Submitted
17 Sep 2016
Accepted
19 Oct 2016
First published
20 Oct 2016

Org. Chem. Front., 2017,4, 81-85
Article type
Research Article

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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