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

Authors

Dennis Wiedenhoeft, Marquette UniversityFollow
Adam R. Benoit, Marquette University
Jacob D. Porter, Marquette University
Yibiao Wu, Marquette University
Rajdeep S. Virdi, Marquette University
Alaa Shanaa, Marquette University
Chris Dockendorff, Marquette UniversityFollow

Document Type

Article

Language

eng

Format of Original

10 p.

Publication Date

2016

Publisher

Thieme Publishing

Source Publication

Synthesis

Source ISSN

0039-7881

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.

Comments

Accepted version. Synthesis, Vol. 48, No. 15 (2016): 2413-2422. DOI. © 2016 Georg Thieme Verlag KG. Used with permission.

Recommended Citation

Wiedenhoeft, Dennis; Benoit, Adam R.; Porter, Jacob D.; Wu, Yibiao; Virdi, Rajdeep S.; Shanaa, Alaa; and Dockendorff, Chris, "Design and Synthesis of Oxazoline-Based Scaffolds for Hybrid Lewis Acid/Lewis Base Catalysis of Carbon–Carbon Bond Formation" (2016). Chemistry Faculty Research and Publications. 570.
https://epublications.marquette.edu/chem_fac/570