Synthesis of fluorinated glutamic acid derivatives via vinylalumination |
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Authors: | P Veeraraghavan Ramachandran Sateesh Madhi |
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Institution: | a Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084, United States b Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202-3274, United States |
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Abstract: | A variety of structural types of fluorinated allylic acetates, prepared by vinylalumination of fluorinated aldehydes, were reacted with the benzophenone imine of glycine tert-butyl ester to provide 4-(fluorobenzylidenyl)- and 4-(fluoroalkylidenyl) glutamic acid derivatives in 61-96% yield. The 4-(4-fluorobenzylidenyl) glutamic acid derivative was hydrolyzed to give the 4-(4-fluorobenzylidenyl)pyroglutamate and then hydrogenated to the 4-(4-fluorobenzyl)pyroglutamate. The catalytic enantioselective conjugate addition-elimination of the benzophenone imine of glycine tert-butyl ester with the fluorinated allylic acetates prepared from fluoral, pentafluorobenzaldehyde, and 2,6-difluorobenzaldehyde provided the corresponding 4-(fluoroalkylidenyl)- and 4-(fluorobenzylidenyl) glutamic acid derivatives in 42, 45 and 80% ee, respectively. |
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Keywords: | Fluorine-containing amino acids Conjugate addition-elimination Glutamates Vinylalumination Excitatory amino acids |
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