Generality-Driven Catalyst Development: A Universal Catalyst for Enantioselective Nitroalkene Reduction
Zihang Deng, Melanie A. Padalino, Julius E. L. Jan, Sangjun Park, Michael W. Danneman, Jeffrey N. Johnston*
*Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235, United States,
Email: jeffrey.n.johnston
vanderbilt.edu
Z. Deng, M. A. Padalino, J. E. L. Jan, S. Park, M. W. Danneman, J. N. Johnston, J. Am. Chem. Soc., 2024, 146, 1269-1275.
DOI: 10.1021/jacs.3c12436
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Abstract
An organocatalyst delivers nitroalkanes from β,β-disubstituted nitroalkenes with a generality otherwise achievable only by a combination of several organo- and organometallic catalysts. The catalyst improves yield and/or enantioselection of the reduction of some major classes of nitroalkenes.
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General procedure for enantioselective reduction of β,β-disubstituted nitroalkenes
A flame-dried vial was charged with β,β-disubstituted nitroalkene, catalyst (5 - 10 mol%), and dry toluene (0.1 M). The solution was pre-cooled in a freezer at 0 °C for an hour, then Hantzsch ester (1.6 equiv) was added to the vial. The vial was evacuated and backfilled with argon and stirred at 0 °C for 48 - 96 h. The reaction mixture was filtered through a silica plug, eluting with hexanes/DCM (10:1) to yield the desired nitroalkane unless noted otherwise. The enantiomeric excess was determined by chiral HPLC.
Key Words
reduction of α,β-unsaturated compounds, reduction of enamines, Hantzsch ester, organocatalysis
ID: J48-Y2024
