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. 2021 May 3;60(19):10542-10546.
doi: 10.1002/anie.202102694. Epub 2021 Mar 30.

Ethanol: Unlocking an Abundant Renewable C2 -Feedstock for Catalytic Enantioselective C-C Coupling

Cole C Meyer  1 , Nicholas P Stafford  1 , Melinda J Cheng  1 , Michael J Krische  1
Affiliations

Ethanol: Unlocking an Abundant Renewable C2 -Feedstock for Catalytic Enantioselective C-C Coupling

Cole C Meyer et al. Angew Chem Int Ed Engl. .

Abstract

With annual production at >85 million tons/year, ethanol is the world's largest-volume renewable small molecule carbon source, yet its use as a C2 -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.

Keywords: enantioselectivity; ethanol; hydrogen transfer; iridium; renewable sources.

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Figures

Figure 1.
Figure 1.
Opportunities for ethanol-based chemical manufacture.
Scheme 1.
Scheme 1.
Selected optimization experiments in the enantioselective π-allyliridium-C,O-benzoate-catalyzed coupling of ethanol with allylic acetate 1a and general mechanism.a aYields are of material isolated by silica gel chromatography. Enantioselectivities were determined by chiral stationary phase HPLC analysis. See Supporting Information for further experimental details.
Scheme 2.
Scheme 2.
Representative phenethyl amines and conversion of ethanol adducts to phenethylamines 5a-5f.a aYields are of material isolated by silica gel chromatography. Enantioselectivities were determined by chiral stationary phase HPLC analysis. See Supporting Information for further experimental details.
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