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Organocatalyzed asymmetric formal [3 + 2] cycloaddition of isocyanoacetates with N-itaconimides: facile access to optically active spiropyrroline succinimide derivatives

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Abstract

An efficient organocatalytic asymmetric formal [3 + 2] cycloaddition reaction of α-aryl isocyanoacetates with N-aryl or alkyl substituted itaconimides catalyzed by a dihydroquinine derived squaramide catalyst has been investigated, which affords the corresponding spiropyrroline succinimide derivatives with two non-adjacent quaternary–quaternary stereocenters in moderate to good yields (up to 82%) with moderate to excellent diastereoselectivities (up to >20 : 1 dr) and excellent enantioselectivities (90–>99% ee) under mild conditions.

Graphical abstract: Organocatalyzed asymmetric formal [3 + 2] cycloaddition of isocyanoacetates with N-itaconimides: facile access to optically active spiropyrroline succinimide derivatives

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Publication details

The article was received on 25 Jul 2019, accepted on 16 Oct 2019 and first published on 17 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QO00939F
Org. Chem. Front., 2019, Advance Article

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    Organocatalyzed asymmetric formal [3 + 2] cycloaddition of isocyanoacetates with N-itaconimides: facile access to optically active spiropyrroline succinimide derivatives

    M. Zhao, Q. Liu, K. Yu, X. Zhao and M. Shi, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00939F

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