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Start Over Author "Jakowiecki, Jakub" Topic amino acids Language english
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1. Synthesis of alpha-trifluoromethyl-beta-lactams and esters of beta-amino acids via 1,3-dipolar cycloaddition of nitrones to fluoroalkenes.

Author

Jakowiecki J, Loska R, and Makosza M

Subjects
Alkenes chemistry, Esters chemistry, Fluorine Compounds chemistry, Hydrogen-Ion Concentration, Isoxazoles chemistry, Methylation, Molecular Structure, Oxidation-Reduction, Oxides chemistry, Oxygen chemistry, Stereoisomerism, beta-Lactams chemistry, Alkenes chemical synthesis, Amino Acids chemistry, Esters chemical synthesis, Fluorine Compounds chemical synthesis, Nitrogen Oxides chemistry, beta-Lactams chemical synthesis
Abstract

Nitrones derived from aromatic or aliphatic aldehydes or ketones react with hexafluoropropene (HFP) or 2H-pentafluoropropene (PFP) to give the respective fluorinated isoxazolidine derivatives in good yields with complete regioselectivity and moderate diastereoselectivity. Catalytic hydrogenolysis of the N-O bond under ambient pressure and temperature leads to fluorides of beta-amino acids that undergo cyclization to alpha-trifluoromethylated beta-lactams or, under acidic conditions, form esters of alpha-trifluoromethylated beta-amino acids.

Published
2008
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