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Synlett 2018; 29(10): 1272-1280
DOI: 10.1055/s-0036-1591870
DOI: 10.1055/s-0036-1591870
synpacts
Weinreb β-Ketoamides in Enantioselective Organocatalysis: A Balance between Reactivity and Selectivity
Haiying Du
Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France eMail: xavier.bugaut@univ-amu.fr
,
Yohan Dudognon
Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France eMail: xavier.bugaut@univ-amu.fr
,
Jean Rodriguez
Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France eMail: xavier.bugaut@univ-amu.fr
,
Thierry Constantieux
Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France eMail: xavier.bugaut@univ-amu.fr
,
Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France eMail: xavier.bugaut@univ-amu.fr
› InstitutsangabenFinancial support from Aix Marseille Université, Centrale Marseille, and the CNRS, along with scholarships from the China Scholarship Council (H.Y.D.) and the Ministère de l’Enseignement Supérieur et de la Recherche (Y.D.) are acknowledged.Weitere Informationen
Publikationsverlauf
Received: 03. November 2017
Accepted after revision: 20. November 2017
Publikationsdatum:
03. Januar 2018 (online)
Published as part of the Special Section 9th EuCheMS Organic Division Young Investigator Workshop
Abstract
β-Dicarbonyl compounds have established themselves as substrates of choice in enantioselective organocatalysis because of their easy activation. Among them, β-diketones, β-diesters, and β-ketoesters lead the dance and there has been only limited work with other β-dicarbonyl compounds as pronucleophiles. In this Synpacts article, we wish to discuss our recent contributions to the introduction of Weinreb β-ketoamides in organocatalyzed transformations, where they can provide an interesting balance between reactivity and selectivity, with also interesting potentialities in terms of postfunctionalization.
1 Introduction
2 Preparation of Weinreb β-Ketoamides
3 Michael Addition to Nitroolefins
4 Multicomponent Synthesis of Tetrahydropyridines
5 Outlook
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Selected examples:
For selected examples, see:
For selected examples, see:
For a related study with other tertiary β-ketoamides in the presence of a bifunctional supported iminophosphorane-thiourea catalyst, see:
For unsuccessful attempts in the presence of proline, see:
For a recent highly efficient and selective variant, see:
For selected reviews, see:
For selected examples, see:
For selected other related strategies for the synthesis of 1,4,5,6,-tetrahydripyridines, see:
For other organocatalyzed synthetic routes towards 1,2,3,4-tetrahydropyridines, see:
