Synthesis 2016; 48(15): 2413-2422
DOI: 10.1055/s-0035-1560436
paper
© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 04 March 2016

Accepted: 09 March 2016

Publication Date:
04 April 2016 (online)


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.

Supporting Information

 
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