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 without racemization at the stereogenic center of the amino acid.
Lehrstuhl für Organische Chemie I and Catalysis Research Center (CRC), Technische Universität München , Lichtenbergstrasse 4, 85747 Garching, Germany.
Harish Kumar
HK
Potukuchi
Thorsten
T
Bach
D000478:Alkylation; D002384:Catalysis; D015394:Molecular Structure; D009636:Norbornanes / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
D009636:Norbornanes; D009942:Organometallic Compounds; D010165:Palladium; D014364:Tryptophan