Literature DB >> 16433519

Catalytic asymmetric Pictet-Spengler reaction.

Jayasree Seayad1, Abdul Majeed Seayad, Benjamin List.   

Abstract

A catalytic asymmetric Pictet-Spengler reaction has been developed, wherein treating substituted tryptamines with an aldehyde in the presence of a catalytic amount of a chiral phosphoric acid provides the corresponding tetrahydro-beta-carboline derivatives in high yields and enantiomeric excesses. The reaction works well with both aliphatic and aromatic aldehydes.

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Year:  2006        PMID: 16433519     DOI: 10.1021/ja057444l

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


  36 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.  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

4.  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

5.  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 6.  Natural products as inspiration for the development of asymmetric catalysis.

Authors:  Justin T Mohr; Michael R Krout; Brian M Stoltz
Journal:  Nature       Date:  2008-09-18       Impact factor: 49.962

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.  Catalytic stereoselective synthesis of diverse oxindoles and spirooxindoles from isatins.

Authors:  Jacob P MacDonald; Joseph J Badillo; Gary E Arevalo; Abel Silva-García; Annaliese K Franz
Journal:  ACS Comb Sci       Date:  2012-04-02       Impact factor: 3.784

9.  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

10.  A tandem isomerization/prins strategy: iridium(III)/Brønsted acid cooperative catalysis.

Authors:  Vince M Lombardo; Christopher D Thomas; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-11       Impact factor: 15.336

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