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Issue 73, 2020
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Enantioselective construction of dispirotriheterocycles featuring a 4-aminopyrazolone motif through a cascade Michael/cyclization process

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Abstract

A highly efficient and asymmetric process to achieve spirocyclic 4-aminopyrazolone derivatives through a cascade Michael addition/cyclization reaction of 4-isothiocyanato pyrazolones with 3-ylideneoxindoles was developed. This reaction forged multicyclic dispiro[pyrazolone-pyrrolidinethione-oxindole] core structures bearing three contiguous stereogenic centers, including two spiro-quaternary stereocenters with excellent diastereo- and enantioselectivities (up to 99% ee, >20 : 1 dr). The product can be readily diversified to expand the chemical space of spiropyrazolone species. A plausible mechanism to account for the stereochemical course of the cascade process was proposed.

Graphical abstract: Enantioselective construction of dispirotriheterocycles featuring a 4-aminopyrazolone motif through a cascade Michael/cyclization process

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Article information


Submitted
17 Jun 2020
Accepted
04 Aug 2020
First published
05 Aug 2020

Chem. Commun., 2020,56, 10690-10693
Article type
Communication

Enantioselective construction of dispirotriheterocycles featuring a 4-aminopyrazolone motif through a cascade Michael/cyclization process

S. Wei, X. Bao, W. Wang, S. Nawaz, Q. Dai, J. Qu and B. Wang, Chem. Commun., 2020, 56, 10690
DOI: 10.1039/D0CC04215C

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