Literature DB >> 15327311

Highly enantioselective catalytic acyl-pictet-spengler reactions.

Mark S Taylor1, Eric N Jacobsen.   

Abstract

The enantioselective cyclization of N-acyliminium ions generated in situ from tryptamine is promoted with high enantioselectivity by a new chiral thiourea catalyst. This represents the first successful system for asymmetric catalysis of the Pictet-Spengler reaction.

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Year:  2004        PMID： 15327311     DOI： 10.1021/ja046259p

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


  56 in total

1.  Electronically Rich N-Substituted Tetrahydroisoquinoline 3-Carboxylic Acid Esters: Concise Synthesis and Conformational Studies.

Authors:  Rami A Al-Horani; Umesh R Desai
Journal:  Tetrahedron       Date:  2012-01-10       Impact factor: 2.457

2.  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

3.  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

4.  Attractive noncovalent interactions in asymmetric catalysis: links between enzymes and small molecule catalysts.

Authors:  Robert R Knowles; Eric N Jacobsen
Journal:  Proc Natl Acad Sci U S A       Date:  2010-10-18       Impact factor: 11.205

5.  Total synthesis of enantiopure phalarine via a stereospecific Pictet-Spengler reaction: traceless transfer of chirality from L-tryptophan.

Authors:  John D Trzupek; Dongjoo Lee; Brendan M Crowley; Vasilios M Marathias; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

6.  Acid-promoted cyclization reactions of tetrahydroindolinones. Model studies for possible application in a synthesis of selaginoidine.

Authors:  Mickea D Rose; Michael P Cassidy; Paitoon Rashatasakhon; Albert Padwa
Journal:  J Org Chem       Date:  2007-01-19       Impact factor: 4.354

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

Authors:  Rebekka S Klausen; Eric N Jacobsen
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

8.  Direct modification of the proinflammatory cytokine macrophage migration inhibitory factor by dietary isothiocyanates.

Authors:  Kristin K Brown; Frances H Blaikie; Robin A J Smith; Joel D A Tyndall; Hongqi Lue; Jürgen Bernhagen; Christine C Winterbourn; Mark B Hampton
Journal:  J Biol Chem       Date:  2009-09-23       Impact factor: 5.157

9.  Mechanism of amido-thiourea catalyzed enantioselective imine hydrocyanation: transition state stabilization via multiple non-covalent interactions.

Authors:  Stephan J Zuend; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2009-10-28       Impact factor: 15.419

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

Authors:  Qingyang Zhao; Jialin Wen; Renchang Tan; Kexuan Huang; Pedro Metola; Rui Wang; Eric V Anslyn; Xumu Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-18       Impact factor: 15.336
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