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Issue 36, 2016
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Organocatalytic cascade Michael/Michael reaction for the asymmetric synthesis of spirooxindoles containing five contiguous stereocenters

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Abstract

A bifunctional squaramide-catalyzed Michael/Michael cascade reaction for the construction of five-membered spirooxindoles was developed. This reaction afforded the corresponding products with five contiguous stereocenters including a quaternary center in good to excellent yields (up to 93%) with excellent stereoselectivities (up to >99 : 1 dr, 98% ee). Meanwhile, the practicality of this methodology was illustrated by a gram-scale synthesis, one-pot four-component reaction and synthetic transformation of the resulting adduct.

Graphical abstract: Organocatalytic cascade Michael/Michael reaction for the asymmetric synthesis of spirooxindoles containing five contiguous stereocenters

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Publication details

The article was received on 26 Jan 2016, accepted on 29 Mar 2016 and first published on 30 Mar 2016


Article type: Communication
DOI: 10.1039/C6CC00705H
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Chem. Commun., 2016,52, 6162-6165

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    Organocatalytic cascade Michael/Michael reaction for the asymmetric synthesis of spirooxindoles containing five contiguous stereocenters

    B. Zhao and D. Du, Chem. Commun., 2016, 52, 6162
    DOI: 10.1039/C6CC00705H

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