AI Article Synopsis
- A Mannich reaction was developed using α-amino acid-derived azlactones and isatin-derived ketimines, facilitated by a chiral bifunctional squaramide organocatalyst.
- The reaction produced α,β-diamino acid derivatives with varying yields (40-95%), and showed moderate to excellent diastereoselectivity (3:1 to 20:1) and enantioselectivity (66-97%).
- This method is practical for larger-scale production, allowing easy conversion of the Mannich adduct into α,β-diamino esters with simple processes.
Article Abstract
A highly stereoselective Mannich reaction of α-amino acid derived azlactones with isatin-derived ketimines enabled by a chiral bifunctional squaramide organocatalyst is reported, affording α,β-diamino acid derivatives bearing vicinal quaternary stereocenters in moderate to good yields (40-95%), moderate to excellent diastereoselectivities (3:1 → 20:1), and good to excellent enantioselectivities (66-97%). This reaction can be readily performed on gram scale, and the Mannich adduct could be easily converted to the corresponding α,β-diamino ester via simple operations.
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| http://dx.doi.org/10.1021/acs.joc.9b03000 | DOI Listing |
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