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Ethanol: Unlocking an Abundant Renewable C<sub>2</sub>‐Feedstock for Catalytic Enantioselective C−C Coupling

Cole C. Meyer, Nicholas P. Stafford, Melinda J. Cheng, Michael J. Krische

2021Angewandte Chemie International Edition27 citationsDOIOpen Access PDF

Abstract

Abstract With annual production at &gt;85 million tons/year, ethanol is the world's largest‐volume renewable small molecule carbon source, yet its use as a C 2 ‐feedstock in enantioselective C−C coupling is unknown. Here, the first catalytic enantioselective C−C couplings of ethanol are demonstrated in reactions with structurally complex, nitrogen‐rich allylic acetates incorporating the top 10 N‐heterocycles found in FDA‐approved drugs.

Topics & Concepts

Enantioselective synthesisRaw materialEthanolCatalysisAllylic rearrangementChemistryOrganic chemistryAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis