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Synlett 2001; 2001(8): 1287-1289
DOI: 10.1055/s-2001-16054
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α-Fluoromethyl Tryptophans via Imino Ene Reaction

Sergej N. Osipov* , Natalia M. Kobel'kova, Alexey F. Kolomiets, Ksenia Pumpor, Beate Koksch, Klaus Burger
  • *A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Science, Vavilov str. 28, 117813 Moscow, GSP-1, Russia; Fax (49) 341 9 73 65 99; E-mail: burger@organik.chem.uni-leipzig.de
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Publikationsdatum:
31. Dezember 2001 (online)

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A preparative simple synthesis of α-fluoromethyl tryptophans is described. The new method is based on a non-catalytic imine ene reaction of highly electrophilic imines derived from methyl bromodifluoro- and trifluoropyruvate, and 1-sulfonyl-3-methylene indolines.

α-fluoromethyl substituted α-amino acids - tryptophans - 3-methylene indoles - fluorinated imines - ene reactions