Literature DB >> 30262933

Functionalized Cyclopentanes via Sc(III)-Catalyzed Intramolecular Enolate Alkylation.

Christopher C McAtee1, Duncan C Ellinwood1, Rory C McAtee1, Corinna S Schindler1.   

Abstract

We report herein the intramolecular α-tert-alkylation of unsaturated β-ketoesters which gives rise to highly functionalized cyclopentanes. This strategy is characterized by its operational simplicity, mild reaction conditions and the use of scandium(III) triflate as a Lewis acid catalyst. Of interest, cyclopentanes bearing heterocycles, sites for post reaction functionalization and spirocyclic architectures are accessible with this strategy.

Entities:  

Keywords:  Lewis acid catalysis; Scandium(III) triflate; enolate alkylation; functionalized cyclopentanes

Year:  2018        PMID: 30262933      PMCID: PMC6152925          DOI: 10.1016/j.tet.2018.04.036

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  12 in total

1.  Rare-earth metal triflates in organic synthesis.

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Review 2.  Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors:  Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
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4.  Mechanistic Investigations of the Iron(III)-Catalyzed Carbonyl-Olefin Metathesis Reaction.

Authors:  Jacob R Ludwig; Susan Phan; Christopher C McAtee; Paul M Zimmerman; James J Devery; Corinna S Schindler
Journal:  J Am Chem Soc       Date:  2017-07-28       Impact factor: 15.419

5.  Synthesis of potential ambra odorants: 5,5,9-trimethyldecalyl derivatives.

Authors:  G Ohloff; F Näf; R Decorzant; W Thommen; E Sundt
Journal:  Helv Chim Acta       Date:  1973-06-06       Impact factor: 2.164

6.  Catalytic enantioselective Conia-ene reaction.

Authors:  Britton K Corkey; F Dean Toste
Journal:  J Am Chem Soc       Date:  2005-12-14       Impact factor: 15.419

7.  Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl-Olefin Metathesis.

Authors:  Christopher C McAtee; Paul S Riehl; Corinna S Schindler
Journal:  J Am Chem Soc       Date:  2017-02-21       Impact factor: 15.419

8.  Gold(I)-catalyzed Conia-ene reaction of beta-ketoesters with alkynes.

Authors:  Joshua J Kennedy-Smith; Steven T Staben; F Dean Toste
Journal:  J Am Chem Soc       Date:  2004-04-14       Impact factor: 15.419

9.  Iron(III)-catalysed carbonyl-olefin metathesis.

Authors:  Jacob R Ludwig; Paul M Zimmerman; Joseph B Gianino; Corinna S Schindler
Journal:  Nature       Date:  2016-04-27       Impact factor: 49.962

10.  Manifestation of polar reaction pathways of 2,3-dichloro-5,6-dicyano-p-benzoquinone.

Authors:  Xingwei Guo; Herbert Mayr
Journal:  J Am Chem Soc       Date:  2013-08-12       Impact factor: 15.419

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  1 in total

Review 1.  Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances.

Authors:  Thiago S Silva; Fernando Coelho
Journal:  Beilstein J Org Chem       Date:  2021-07-07       Impact factor: 2.883

  1 in total

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