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

Content Provider	Semantic Scholar
Author	Wiedenhoeft, Dennis Benoit, Adam Porter, Jacob D. Wu, Yibiao Virdi, Rajdeep S. Shanaa, Alaa Dockendorff, Chris
Copyright Year	2016
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.
Starting Page	2413
Ending Page	2422
Page Count	10
File Format	PDF HTM / HTML
DOI	10.1055/s-0035-1560436
Volume Number	48
Alternate Webpage(s)	https://epublications.marquette.edu/cgi/viewcontent.cgi?article=1572&context=chem_fac
Alternate Webpage(s)	https://doi.org/10.1055/s-0035-1560436
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article