Selective C‑2 Alkylation of Tryptophan by a Pd(II)/Norbornene-Promoted C–H Activation Reaction

A palladium(II)-catalyzed norbornene-mediated regioselective alkylation at the C-2 indole position of N-tert-butyloxycarbonyl (Boc)-protected (S)-tryptophan ethyl ester is reported. The protocol employs mild reaction conditions and is tolerant of a range of functional groups. The reaction proceeds w...

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Veröffentlicht in:Journal of organic chemistry 2013-12, Vol.78 (23), p.12263-12267
Hauptverfasser: Potukuchi, Harish Kumar, Bach, Thorsten
Format: Artikel
Sprache:eng
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Zusammenfassung:A palladium(II)-catalyzed norbornene-mediated regioselective alkylation at the C-2 indole position of N-tert-butyloxycarbonyl (Boc)-protected (S)-tryptophan ethyl ester is reported. The protocol employs mild reaction conditions and is tolerant of a range of functional groups. The reaction proceeds without racemization at the stereogenic center of the amino acid.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo402107m