Bifunctional Squaramide-Catalyzed Asymmetric [3 + 2] Cyclization of 2‑(1-Methyl-2-oxoindolin-3-yl)malononitriles with Unsaturated Pyrazolones To Construct Spirooxindole-Fused Spiropyrazolones
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 ca...
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| Published in | Journal of organic chemistry Vol. 84; no. 16; pp. 10209 - 10220 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
16.08.2019
Amer Chemical Soc |
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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. |
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| AbstractList | 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. 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. |
| Author | Lin, Ye Zhao, Bo-Liang Du, Da-Ming |
| AuthorAffiliation | School of Chemistry and Chemical Engineering |
| AuthorAffiliation_xml | – name: School of Chemistry and Chemical Engineering |
| Author_xml | – sequence: 1 givenname: Ye orcidid: 0000-0002-7784-539X surname: Lin fullname: Lin, Ye – sequence: 2 givenname: Bo-Liang surname: Zhao fullname: Zhao, Bo-Liang – sequence: 3 givenname: Da-Ming orcidid: 0000-0002-9924-5117 surname: Du fullname: Du, Da-Ming email: dudm@bit.edu.cn |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31318546$$D View this record in MEDLINE/PubMed |
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| Keywords | BISPIROOXINDOLES HETEROCYCLES ENANTIOSELECTIVE CONSTRUCTION DERIVATIVES ACCESS SPIROCYCLOPENTANE OXINDOLES |
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| Snippet | The present paper reports a highly stereoselective synthesis of spirooxindole-fused spiropyrazolones through the asymmetric [3 + 2] cyclization reaction of... |
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| SubjectTerms | catalysts catalytic activity chemical structure Chemistry Chemistry, Organic cyclization reactions organic chemistry Physical Sciences pyrazolones Science & Technology stereoselective synthesis |
| Title | Bifunctional Squaramide-Catalyzed Asymmetric [3 + 2] Cyclization of 2‑(1-Methyl-2-oxoindolin-3-yl)malononitriles with Unsaturated Pyrazolones To Construct Spirooxindole-Fused Spiropyrazolones |
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