Design and Synthesis of Oxazoline-Based Scaffolds for Hybrid Lewis Acid/Lewis Base Catalysis of Carbon–Carbon Bond Formation

Dennis Wiedenhoeft; Adam R. Benoit; Jacob D. Porter; Yibiao Wu; Rajdeep S. Virdi; Alaa Shanaa; Chris Dockendorff

doi:10.1055/s-0035-1560436

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(15): 2413-2422
DOI: 10.1055/s-0035-1560436

paper

Design and Synthesis of Oxazoline-Based Scaffolds for Hybrid Lewis Acid/Lewis Base Catalysis of Carbon–Carbon Bond Formation

Dennis Wiedenhoeft

Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, WI, 53201-1881, USA eMail: christopher.dockendorff@mu.edu

,

Adam R. Benoit

Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, WI, 53201-1881, USA eMail: christopher.dockendorff@mu.edu

,

Jacob D. Porter

Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, WI, 53201-1881, USA eMail: christopher.dockendorff@mu.edu

,

Yibiao Wu

Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, WI, 53201-1881, USA eMail: christopher.dockendorff@mu.edu

,

Rajdeep S. Virdi

Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, WI, 53201-1881, USA eMail: christopher.dockendorff@mu.edu

,

Alaa Shanaa

Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, WI, 53201-1881, USA eMail: christopher.dockendorff@mu.edu

,

Chris Dockendorff*

Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, WI, 53201-1881, USA eMail: christopher.dockendorff@mu.edu

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Abstract

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This manuscript is dedicated to the memory of Prof. Keith Fagnou, whose curiosity, enthusiasm, and insights continue to inspire us.

Abstract

A new class of hybrid Lewis acid/Lewis base catalysts has been designed and prepared with an initial objective of promoting stereoselective direct aldol reactions. Several scaffolds were synthesized that contain amine moieties capable of enamine catalysis, connected to heterocyclic metal-chelating sections composed of an oxazole–oxazoline or thiazole–oxazoline. Early screening results have identified oxazole–oxazoline-based systems capable of promoting a highly diastereo- and enantioselective direct aldol reaction of propionaldehyde with 4-nitrobenzaldehyde, when combined with Lewis acids such as zinc triflate.

Key words

hybrid catalysis - aldol reaction - organocatalysis - Lewis acids - oxazoline - asymmetric catalysis

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Referenzen

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