Literature DB >> 18815709

Highly enantioselective organocatalytic formation of a quaternary carbon center via chiral Brønsted acid catalyzed self-coupling of enamides.

Christine Baudequin1, Alexandru Zamfir, Svetlana B Tsogoeva.   

Abstract

The enantioselective BINOL-phosphate catalyzed formation of a quaternary carbon center, bearing a N-atom has been achieved through the self-coupling reaction of enamides; the corresponding products have been isolated in up to >99% ee and their application for the synthesis of versatile synthetic building blocks-beta-aminoketones-has been demonstrated.

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Year:  2008        PMID: 18815709     DOI: 10.1039/b804477e

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  5 in total

1.  Proline Sulfonamide-Based Organocatalysis: Better Late than Never.

Authors:  Hua Yang; Rich G Carter
Journal:  Synlett       Date:  2010-09-01       Impact factor: 2.454

2.  Chiral Brønsted Acid-Catalyzed Enantioselective α-Amidoalkylation Reactions: A Joint Experimental and Predictive Study.

Authors:  Eider Aranzamendi; Sonia Arrasate; Nuria Sotomayor; Humberto González-Díaz; Esther Lete
Journal:  ChemistryOpen       Date:  2016-11-23       Impact factor: 2.911

3.  Selecting Chiral BINOL-Derived Phosphoric Acid Catalysts: General Model To Identify Steric Features Essential for Enantioselectivity.

Authors:  Jolene P Reid; Jonathan M Goodman
Journal:  Chemistry       Date:  2017-09-14       Impact factor: 5.236

4.  Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions.

Authors:  Jing-Yu Guo; Ze-Yu Zhang; Ting Guan; Lei-Wen Mao; Qian Ban; Kai Zhao; Teck-Peng Loh
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

5.  Asymmetric synthesis of highly functionalized tetrahydropyrans via a one-pot organocatalytic Michael/Henry/ketalization sequence.

Authors:  Robert Hahn; Gerhard Raabe; Dieter Enders
Journal:  Org Lett       Date:  2014-06-27       Impact factor: 6.005

  5 in total

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