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- Publisher Website: 10.1021/acs.joc.9b02176
- Scopus: eid_2-s2.0-85075580822
- PMID: 31702146
- WOS: WOS:000502170600061
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Article: Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentenes Containing a Quaternary Chiral Center via a Thiosquaramide-Catalyzed Cascade Michael-Henry Reaction
Title | Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentenes Containing a Quaternary Chiral Center via a Thiosquaramide-Catalyzed Cascade Michael-Henry Reaction |
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Authors | |
Issue Date | 2019 |
Citation | Journal of Organic Chemistry, 2019, v. 84 n. 23, p. 15655-15661 How to Cite? |
Abstract | © 2019 American Chemical Society. An efficient method for the highly diastereoselective synthesis of chiral quaternary center-containing cyclopentenes via a cinchona alkaloid-derived thiosquaramide VIII-catalyzed tandem Michael-Henry reaction of phenacylmalononitriles and nitroolefins was deleveloped. Meanwhile, up to 98% of enantioselectivity was observed. A mechanism involving thiosqaramide-catalyzed asymmetric Michael addition and assisted E2 elimination was proposed based on experimental data and preliminary theoretical analysis (Hartree-Fock calculations). |
Persistent Identifier | http://hdl.handle.net/10722/292134 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Chen, Chen | - |
dc.contributor.author | Wei, Ran | - |
dc.contributor.author | Yi, Xing | - |
dc.contributor.author | Gao, Li | - |
dc.contributor.author | Zhang, Min | - |
dc.contributor.author | Liu, Han | - |
dc.contributor.author | Li, Qingshan | - |
dc.contributor.author | Song, Heng | - |
dc.contributor.author | Ban, Shurong | - |
dc.date.accessioned | 2020-11-17T14:55:50Z | - |
dc.date.available | 2020-11-17T14:55:50Z | - |
dc.date.issued | 2019 | - |
dc.identifier.citation | Journal of Organic Chemistry, 2019, v. 84 n. 23, p. 15655-15661 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10722/292134 | - |
dc.description.abstract | © 2019 American Chemical Society. An efficient method for the highly diastereoselective synthesis of chiral quaternary center-containing cyclopentenes via a cinchona alkaloid-derived thiosquaramide VIII-catalyzed tandem Michael-Henry reaction of phenacylmalononitriles and nitroolefins was deleveloped. Meanwhile, up to 98% of enantioselectivity was observed. A mechanism involving thiosqaramide-catalyzed asymmetric Michael addition and assisted E2 elimination was proposed based on experimental data and preliminary theoretical analysis (Hartree-Fock calculations). | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of Organic Chemistry | - |
dc.title | Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentenes Containing a Quaternary Chiral Center via a Thiosquaramide-Catalyzed Cascade Michael-Henry Reaction | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/acs.joc.9b02176 | - |
dc.identifier.pmid | 31702146 | - |
dc.identifier.scopus | eid_2-s2.0-85075580822 | - |
dc.identifier.volume | 84 | - |
dc.identifier.issue | 23 | - |
dc.identifier.spage | 15655 | - |
dc.identifier.epage | 15661 | - |
dc.identifier.eissn | 1520-6904 | - |
dc.identifier.isi | WOS:000502170600061 | - |
dc.identifier.issnl | 0022-3263 | - |