Literature DB >> 19222080

Highly enantioselective Pictet-Spengler reactions with alpha-ketoamide-derived ketimines: access to an unusual class of quaternary alpha-amino amides.

Farhan R Bou-Hamdan1, James L Leighton.   

Abstract

"Quat's" the story? N-Aryl amides are effective directing/activating groups for chlorosilane Lewis acids. This aspect has been exploited for the development of the first simple and general method for the highly enantioselective Pictet-Spengler reaction of ketimines derived from alpha-ketoamides leading to quaternary alpha-amino acid derivatives (see scheme).

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Year:  2009        PMID： 19222080     DOI： 10.1002/anie.200806110

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  7 in total

1.  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

2.  Biocatalytic asymmetric formation of tetrahydro-β-carbolines.

Authors:  Peter Bernhardt; Aimee R Usera; Sarah E O'Connor
Journal:  Tetrahedron Lett       Date:  2010-08-18       Impact factor: 2.415

3.  Highly enantioselective Mannich reactions with α-aryl silyl ketene acetals and imines.

Authors:  Gregory T Notte; Jenny M Baxter Vu; James L Leighton
Journal:  Org Lett       Date:  2011-01-14       Impact factor: 6.005

4.  Total Synthesis of (+)-Arborisidine.

Authors:  Zhiyao Zhou; Alison X Gao; Scott A Snyder
Journal:  J Am Chem Soc       Date:  2019-05-02       Impact factor: 15.419

5.  Copper-catalyzed synthesis of α-ketoamides using water and dioxygen as the oxygen source.

Authors:  Yuanyuan Xiao; Zijuan Yi; Xianyong Yu; Fang Xiao
Journal:  RSC Adv       Date:  2020-08-06       Impact factor: 4.036

6.  Catalytic Enantioselective Pictet-Spengler Reaction of α-Ketoamides Catalyzed by a Single H-Bond Donor Organocatalyst.

Authors:  Rémi Andres; Qian Wang; Jieping Zhu
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-11       Impact factor: 16.823

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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