Literature DB >> 21848300

Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions.

Noah Z Burns1, Michael R Witten, Eric N Jacobsen.   

Abstract

A new method for effecting catalytic enantioselective intramolecular [5 + 2] cycloadditions based on oxidopyrylium intermediates is reported. The dual catalyst system consists of a chiral primary aminothiourea and a second achiral thiourea. Experimental evidence points to a new type of cooperative catalysis with each species being necessary to generate a reactive pyrylium ion pair that undergoes subsequent cycloaddition with high enantioselectivity.

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Year:  2011        PMID： 21848300      PMCID： PMC3173575          DOI： 10.1021/ja206997e

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  35 in total

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4.  Enantioselective Pictet-Spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding.

Authors:  Izzat T Raheem; Parvinder S Thiara; Emily A Peterson; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2007-10-17       Impact factor: 15.419

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6.  Asymmetric cooperative catalysis of strong Brønsted acid-promoted reactions using chiral ureas.

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8.  Studies on oxidopyrylium [5+2] cycloadditions: toward a general synthetic route to the C12-hydroxydaphnetoxins.

Authors:  Paul A Wender; F Christopher Bi; Nicole Buschmann; Francis Gosselin; Cindy Kan; Jung-Min Kee; Hirofumi Ohmura
Journal:  Org Lett       Date:  2006-11-09       Impact factor: 6.005

9.  Englerin A, a selective inhibitor of renal cancer cell growth, from Phyllanthus engleri.

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10.  Catalytic enantioselective intermolecular cycloadditions of 2-diazo-3,6-diketoester-derived carbonyl ylides with alkene dipolarophiles.

Authors:  David M Hodgson; Tobias Brückl; Rebecca Glen; Agnès H Labande; Deborah A Selden; Alexander G Dossetter; Alison J Redgrave
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  39 in total

1.  On- and Off-Cycle Catalyst Cooperativity in Anion-Binding Catalysis.

Authors:  David D Ford; Dan Lehnherr; C Rose Kennedy; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-06-15       Impact factor: 15.419

2.  Mechanistic Studies of Gold and Palladium Cooperative Dual-Catalytic Cross-Coupling Systems.

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Journal:  ACS Catal       Date:  2014-02-07       Impact factor: 13.084

3.  Enantioselective copper-catalyzed alkynylation of benzopyranyl oxocarbenium ions.

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4.  Catalytic Enantioselective Intermolecular [5 + 2] Dipolar Cycloadditions of a 3-Hydroxy-4-pyrone-Derived Oxidopyrylium Ylide.

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Journal:  Org Lett       Date:  2017-11-17       Impact factor: 6.005

5.  Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.

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6.  Enantioselective formal aza-Diels-Alder reactions of enones with cyclic imines catalyzed by primary aminothioureas.

Authors:  Mathieu P Lalonde; Meredeth A McGowan; Naomi S Rajapaksa; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2013-01-28       Impact factor: 15.419

7.  Enantioselective synthesis of 2,2-disubstituted tetrahydrofurans: palladium-catalyzed [3+2] cycloadditions of trimethylenemethane with ketones.

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8.  Rhodium-catalyzed asymmetric hydrogenation of unprotected NH imines assisted by a thiourea.

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Journal:  Angew Chem Int Ed Engl       Date:  2014-06-18       Impact factor: 15.336

9.  Oxidopyrylium [5+2] Cycloaddition Chemistry: Historical Perspective and Recent Advances (2008-2018).

Authors:  Lauren P Bejcek; Ryan P Murelli
Journal:  Tetrahedron       Date:  2018-04-05       Impact factor: 2.457

10.  Mechanistic Studies of Azaphilic versus Carbophilic Activation by Gold(I) in the Gold/Palladium Dual-Catalyzed Rearrangement of Alkenyl Vinyl Aziridines.

Authors:  Joshua J Hirner; Katrina E Roth; Yili Shi; Suzanne A Blum
Journal:  Organometallics       Date:  2012-10-08       Impact factor: 3.876
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