Literature DB >> 19178157

Weak Brønsted acid-thiourea co-catalysis: enantioselective, catalytic protio-Pictet-Spengler reactions.

Rebekka S Klausen1, Eric N Jacobsen.   

Abstract

The development of one-pot imine formation and asymmetric Pictet-Spengler reactions cocatalyzed by a chiral thiourea and benzoic acid is described. Optically active tetrahydro-beta-carbolines, ubiquitous structural motifs in biologically active natural products, are obtained in high ee directly from tryptamine and aldehyde precursors.

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Year:  2009        PMID： 19178157      PMCID： PMC2664157          DOI： 10.1021/ol802887h

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  15 in total

1.  Highly enantioselective catalytic acyl-pictet-spengler reactions.

Authors:  Mark S Taylor; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2004-09-01       Impact factor: 15.419

2.  Stereocontrolled total synthesis of (-)-eudistomin C.

Authors:  Tohru Yamashita; Nobutaka Kawai; Hidetoshi Tokuyama; Tohru Fukuyama
Journal:  J Am Chem Soc       Date:  2005-11-02       Impact factor: 15.419

3.  Indium-mediated asymmetric allylation of acylhydrazones using a chiral urea catalyst.

Authors:  Kian L Tan; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Catalytic asymmetric Pictet-Spengler reaction.

Authors:  Jayasree Seayad; Abdul Majeed Seayad; Benjamin List
Journal:  J Am Chem Soc       Date:  2006-02-01       Impact factor: 15.419

5.  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

6.  Catalytic asymmetric Pictet-Spengler reactions via sulfenyliminium ions.

Authors:  Martin J Wanner; Richard N S van der Haas; Kimberly R de Cuba; Jan H van Maarseveen; Henk Hiemstra
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 7.  Small-molecule H-bond donors in asymmetric catalysis.

Authors:  Abigail G Doyle; Eric N Jacobsen
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

8.  Cooperative Brønsted acid-type organocatalysis: alcoholysis of styrene oxides.

Authors:  Torsten Weil; Mike Kotke; Christian M Kleiner; Peter R Schreiner
Journal:  Org Lett       Date:  2008-03-27       Impact factor: 6.005

Review 9.  Asymmetric catalysis by chiral hydrogen-bond donors.

Authors:  Mark S Taylor; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2006-02-27       Impact factor: 15.336

10.  Mechanistic studies on norcoclaurine synthase of benzylisoquinoline alkaloid biosynthesis: an enzymatic Pictet-Spengler reaction.

Authors:  Louis Y P Luk; Shannon Bunn; David K Liscombe; Peter J Facchini; Martin E Tanner
Journal:  Biochemistry       Date:  2007-08-15       Impact factor: 3.162
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  41 in total

1.  Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; synthesis of dimebolin.

Authors:  Huijun Dong; Regina T Latka; Tom G Driver
Journal:  Org Lett       Date:  2011-04-25       Impact factor: 6.005

2.  Mechanistic studies on the cis to trans epimerization of trisubstituted 1,2,3,4-tetrahydro-beta-carbolines.

Authors:  Michael L Van Linn; James M Cook
Journal:  J Org Chem       Date:  2010-06-04       Impact factor: 4.354

3.  Rh(II)2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides.

Authors:  Ashley L Pumphrey; Huijun Dong; Tom G Driver
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

Review 4.  Methods for 2-Deoxyglycoside Synthesis.

Authors:  Clay S Bennett; M Carmen Galan
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

5.  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

6.  Novel diversity-oriented synthesis-derived respiratory syncytial virus inhibitors identified via a high throughput replicon-based screen.

Authors:  Jeremy R Duvall; Lynn VerPlank; Barbara Ludeke; Sarah M McLeod; Maurice D Lee; Karthick Vishwanathan; Carol A Mulrooney; Sebastian Le Quement; Qin Yu; Michelle A Palmer; Paul Fleming; Rachel Fearns; Michael A Foley; Christina A Scherer
Journal:  Antiviral Res       Date:  2016-04-06       Impact factor: 5.970

7.  Enantioselective Pictet-Spengler Reactions of Isatins for the Synthesis of Spiroindolones.

Authors:  Joseph J Badillo; Abel Silva-García; Benjamin H Shupe; James C Fettinger; Annaliese K Franz
Journal:  Tetrahedron Lett       Date:  2011-10-26       Impact factor: 2.415

8.  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

9.  Study of the cis to trans isomerization of 1-phenyl-2,3-disubstituted tetrahydro-beta-carbolines at C(1). Evidence for the carbocation-mediated mechanism.

Authors:  Hephzibah J Kumpaty; Michael L Van Linn; M Shahjahan Kabir; F Holger Försterling; Jeffrey R Deschamps; James M Cook
Journal:  J Org Chem       Date:  2009-04-03       Impact factor: 4.354

10.  Enantioselective, thiourea-catalyzed intermolecular addition of indoles to cyclic N-acyl iminium ions.

Authors:  Emily A Peterson; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
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