1363260-61-0Relevant academic research and scientific papers
Unified mild reaction conditions for C2-selective Pd-catalysed tryptophan arylation, including tryptophan-containing peptides
Reay, Alan J.,Williams, Thomas J.,Fairlamb, Ian J. S.
, p. 8298 - 8309 (2015/08/03)
Pd-mediated C-H bond functionalisation protocols have been designed and developed on tryptophan derivatives and tryptophan-containing peptides. The examination of different arylation reactions (three sets of different conditions A-C), all of which are notable for their low temperatures (≤40°C), allowed identification of unified and complementary synthetic approaches toward a series of functionalised tryptophan-containing products. Tryptophan-containing peptides demonstrated to be susceptible to aromatic oxidation were successfully and selectively modified through the application of diaryliodonium salts in good yields.
Enantioselective synthesis of tryptophan derivatives by a tandem friedel-crafts conjugate addition/asymmetric protonation reaction
Kieffer, Madeleine E.,Repka, Lindsay M.,Reisman, Sarah E.
supporting information; experimental part, p. 5131 - 5137 (2012/05/05)
The tandem Friedel-Crafts conjugate addition/asymmetric protonation reaction between 2-substituted indoles and methyl 2-acetamidoacrylate is reported. The reaction is catalyzed by (R)-3,3′-dibromo-BINOL in the presence of stoichiometric SnCl4, and is the first example of a tandem conjugate addition/asymmetric protonation reaction using a BINOLSnCl4 complex as the catalyst. A range of indoles furnished synthetic tryptophan derivatives in good yields and high levels of enantioselectivity, even on a preparative scale. The convergent nature of this transformation should lend itself to the preparation of unnatural tryptophan derivatives for use in a broad array of synthetic and biological applications.
