Abstract
A concise and efficient asymmetric Mannich/hemiketalization/retro-Henry cascade reaction between o-hydroxy-α-aminosulfones and α-nitroketones was developed by utilizing a cinchona-derived bifunctional squaramide catalyst. This methodology provided access to β-nitro-substituted amino compounds with up to 95% yield and >99% ee. The practicality was demonstrated by scale-up and diverse derivatizations, including the synthesis of imidazolidinone and amino acid analogs. This is the first report of α-nitroketones in such a cascade reaction, offering a valuable approach for the synthesis of chiral β-nitro amino compounds.
Original language | English |
---|---|
Pages (from-to) | 1877-1888 |
Number of pages | 12 |
Journal | Journal of Organic Chemistry |
Volume | 90 |
Issue number | 5 |
DOIs | |
Publication status | Published - 7 Feb 2025 |