Promotion of Henry reactions using Cu(OTf)2 and a sterically hindered Schiff base: access to enantioenriched β-hydroxynitroalkanes |
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Authors: | Lin Yao Yu Wei Pingan Wang Wei He Shengyong Zhang |
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Institution: | Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Shaanxi Province, Xi''an 710032, PR China |
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Abstract: | The steric and electronic properties of chiral Schiff base ligands derived from cinchona alkaloids were evaluated in asymmetric Henry reactions. Amongst these, the sterically hindered ligand 2 showed outstanding catalytic efficiency in the Cu(II) catalyzed asymmetric addition of nitroalkanes to a variety of aldehydes to afford the desired adducts in high yields (up to 97%) with excellent enantioselectivities (up to 99% ee) and moderate to good diastereoselectivities (up to 84:16 dr). |
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