Bifunctional Squaramide-Catalyzed Asymmetric [3 + 2] Cyclization of 2-(1-Methyl-2-oxoindolin-3-yl)malononitriles with Unsaturated Pyrazolones To Construct Spirooxindole-Fused Spiropyrazolones.

Clicks: 351
ID: 64668
2019
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Abstract
The present paper reports a highly stereoselective synthesis of spirooxindole-fused spiropyrazolones through the asymmetric [3 + 2] cyclization reaction of 2-(1-methyl-2-oxoindolin-3-yl)malononitriles with unsaturated pyrazolones under mild conditions. With only a 1 mol % bifunctional squaramide catalyst, a series of chiral dispirocyclic pyrazolone derivatives were attained in high yields (85-97%) with excellent stereoselectivities (up to >99% ee and in all cases >20:1 dr). Moreover, gram-scale synthesis and further transformation of the products were also demonstrated.
Reference Key
lin2019bifunctionalthe Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Lin, Ye;Zhao, Bo-Liang;Du, Da-Ming;
Journal The Journal of organic chemistry
Year 2019
DOI
10.1021/acs.joc.9b01268
URL
Keywords
luminescence solvent effect heteroleptic zn(ii) complexes

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