File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentenes Containing a Quaternary Chiral Center via a Thiosquaramide-Catalyzed Cascade Michael-Henry Reaction

TitleDiastereo- and Enantioselective Synthesis of Functionalized Cyclopentenes Containing a Quaternary Chiral Center via a Thiosquaramide-Catalyzed Cascade Michael-Henry Reaction
Authors
Chen, ChenWei, RanYi, XingGao, LiZhang, MinLiu, HanLi, QingshanSong, HengBan, Shurong
Issue Date2019
Citation
Journal of Organic Chemistry, 2019, v. 84 n. 23, p. 15655-15661 How to Cite?
DOI: http://dx.doi.org/10.1021/acs.joc.9b02176
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 Identifierhttp://hdl.handle.net/10722/292134
ISSN
0022-3263
2021 Impact Factor: 4.198
2020 SCImago Journal Rankings: 1.200
ISI Accession Number ID
WOS:000502170600061

 

DC FieldValueLanguage
dc.contributor.authorChen, Chen-
dc.contributor.authorWei, Ran-
dc.contributor.authorYi, Xing-
dc.contributor.authorGao, Li-
dc.contributor.authorZhang, Min-
dc.contributor.authorLiu, Han-
dc.contributor.authorLi, Qingshan-
dc.contributor.authorSong, Heng-
dc.contributor.authorBan, Shurong-
dc.date.accessioned2020-11-17T14:55:50Z-
dc.date.available2020-11-17T14:55:50Z-
dc.date.issued2019-
dc.identifier.citationJournal of Organic Chemistry, 2019, v. 84 n. 23, p. 15655-15661-
dc.identifier.issn0022-3263-
dc.identifier.urihttp://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.languageeng-
dc.relation.ispartofJournal of Organic Chemistry-
dc.titleDiastereo- and Enantioselective Synthesis of Functionalized Cyclopentenes Containing a Quaternary Chiral Center via a Thiosquaramide-Catalyzed Cascade Michael-Henry Reaction-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/acs.joc.9b02176-
dc.identifier.pmid31702146-
dc.identifier.scopuseid_2-s2.0-85075580822-
dc.identifier.volume84-
dc.identifier.issue23-
dc.identifier.spage15655-
dc.identifier.epage15661-
dc.identifier.eissn1520-6904-
dc.identifier.isiWOS:000502170600061-
dc.identifier.issnl0022-3263-

Export via OAI-PMH Interface in XML Formats

OR

Export to Other Non-XML Formats