Literature DB >> 10891200

Enantiopure Tetrahydro-beta-carbolines via Pictet-Spengler Reactions with N-Sulfinyl Tryptamines.

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Abstract

The influence of N-sulfinyl chiral auxiliaries on the stereochemistry of the Pictet-Spengler reaction has been investigated. From enantiopure (R)-N-p-toluenesulfinyltryptamine a new and efficient route to enantiopure tetrahydro-beta-carbolines has been established.

Entities:  

Year:  2000        PMID： 10891200     DOI： 10.1021/ol006034t

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


  7 in total

1.  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

2.  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

3.  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

4.  Computational planning of the synthesis of complex natural products.

Authors:  Barbara Mikulak-Klucznik; Patrycja Gołębiowska; Alison A Bayly; Oskar Popik; Tomasz Klucznik; Sara Szymkuć; Ewa P Gajewska; Piotr Dittwald; Olga Staszewska-Krajewska; Wiktor Beker; Tomasz Badowski; Karl A Scheidt; Karol Molga; Jacek Mlynarski; Milan Mrksich; Bartosz A Grzybowski
Journal:  Nature       Date:  2020-10-13       Impact factor: 49.962

Review 5.  The Chiral Pool in the Pictet-Spengler Reaction for the Synthesis of β-Carbolines.

Authors:  Renato Dalpozzo
Journal:  Molecules       Date:  2016-05-27       Impact factor: 4.411

6.  Asymmetric Synthesis of (R)-1-Alkyl-Substituted Tetrahydro-ß-carbolines Catalyzed by Strictosidine Synthases.

Authors:  Desiree Pressnitz; Eva-Maria Fischereder; Jakob Pletz; Christina Kofler; Lucas Hammerer; Katharina Hiebler; Horst Lechner; Nina Richter; Elisabeth Eger; Wolfgang Kroutil
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-21       Impact factor: 15.336

7.  Inverted Binding of Non-natural Substrates in Strictosidine Synthase Leads to a Switch of Stereochemical Outcome in Enzyme-Catalyzed Pictet-Spengler Reactions.

Authors:  Elisabeth Eger; Adam Simon; Mahima Sharma; Song Yang; Willem B Breukelaar; Gideon Grogan; K N Houk; Wolfgang Kroutil
Journal:  J Am Chem Soc       Date:  2020-01-07       Impact factor: 15.419
  7 in total

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