Synlett 2018; 29(10): 1272-1280
DOI: 10.1055/s-0036-1591870
synpacts
© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Financial 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.
Further Information

Publication History

Received: 03 November 2017

Accepted after revision: 20 November 2017

Publication Date:
03 January 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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