Literature DB >> 18802626

Brønsted-acid and Brønsted-base catalyzed Diels-Alder reactions.

Juan Shen1, Choon-Hong Tan.   

Abstract

The enantioselective Diels-Alder reaction is one of the most important reactions for the synthesis of complex molecules. It provides access to chiral six-membered carbocyclic compounds containing up to four stereogenic centers in a single step. Asymmetric catalysis in the Diels-Alder reaction has mainly been realized using chiral Lewis acids. In this perspective, we describe several cases of chiral Brønsted-acid and Brønsted-base catalyzed Diels-Alder reactions, providing an overview of this rapidly growing field.

Entities:  

Year:  2008        PMID: 18802626     DOI: 10.1039/b809505c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  5 in total

1.  Enantioselective Addition of Bromonitromethane to Aliphatic N-Boc Aldimines Using a Homogeneous Bifunctional Chiral Organocatalyst.

Authors:  Kenneth E Schwieter; Jeffrey N Johnston
Journal:  ACS Catal       Date:  2015       Impact factor: 13.084

2.  Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael-Michael-1,2-addition sequence.

Authors:  Pankaj Chauhan; Gregor Urbanietz; Gerhard Raabe; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2014-07-04       Impact factor: 6.222

3.  A Counterion-Directed Approach to the Diels-Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes.

Authors:  Emily Kiss; Craig D Campbell; Russell W Driver; John D Jolliffe; Rosemary Lang; Tetiana Sergeieva; Sergiy Okovytyy; Robert S Paton; Martin D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-07       Impact factor: 15.336

4.  A multi-substrate screening approach for the identification of a broadly applicable Diels-Alder catalyst.

Authors:  Hyejin Kim; Gabriela Gerosa; Jonas Aronow; Pinar Kasaplar; Jie Ouyang; Julia B Lingnau; Paul Guerry; Christophe Farès; Benjamin List
Journal:  Nat Commun       Date:  2019-02-15       Impact factor: 14.919

5.  Enantiodivergent [4+2] Cycloaddition of Dienolates by Polyfunctional Lewis Acid/Zwitterion Catalysis.

Authors:  Vukoslava Miskov-Pajic; Felix Willig; Daniel M Wanner; Wolfgang Frey; René Peters
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-28       Impact factor: 15.336

  5 in total

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