Chiral Brønsted acid catalyzed stereoselective addition of azlactones to 3-vinylindoles for facile access to enantioenriched tryptophan derivatives.
Syn-gled out: The syn diastereo- and enantioselective addition of azlactones to 3-vinylindoles was accomplished by using a chiral, binapthol-derived, Brønsted acid catalyst (see scheme). This method enables facile access to tryptophan derivatives with adjacent quaternary and tertiary stereogenic centers, which are potentially useful for the synthesis of peptidomimetics.
Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan. mterada@m.tohoku.ac.jp
Masahiro
M
Terada
Kenichi
K
Moriya
Kyohei
K
Kanomata
Keiichi
K
Sorimachi
D000143:Acids / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014364:Tryptophan / Q000138:chemical synthesis* / Q000737:chemistry
D000143:Acids; D007211:Indoles; D007783:Lactones; D014364:Tryptophan