10184-96-0Relevant articles and documents
Dearomative indole [5+2] cycloaddition reactions: Stereoselective synthesis of highly functionalized cyclohepta[b]indoles
Mei, Guangjian,Yuan, Hao,Gu, Yueqing,Chen, Wei,Chung, Lung Wa,Li, Chuang-Chuang
, p. 11051 - 11055 (2014)
The first dearomative indole [5+2] cycloaddition reaction with an oxidopyrylium ylide resulted in efficient and diastereoselective construction of some highly functionalized and synthetically challenging oxacyclohepta[b]indoles. The protocol proceeds unde
Enantioselective Copper(II)/Box-Catalyzed Synthesis of Chiral β3-Tryptophan Derivatives
Tarasenko, Elena A.,Shestakov, Ivan V.,Rybakov, Victor B.,Beletskaya, Irina P.
, p. 3913 - 3918 (2019)
β-Amino acids and their derivatives are important building blocks for the preparation of various bioactive compounds and materials. We developed a highly efficient method for the synthesis of β3-tryptophan derivatives based on enantioselective Friedel-Crafts alkylation of indoles with phthaloyl-protected aminomethylenemalonate in the presence of chiral Cu(OTf)2/iPrBox complex as a catalyst. A wide range of indoles with electron-donating and electron-withdrawing substituents gave the desired products in high yields (up to 99 %) and excellent enantioselectivities (up to 99 % ee). In the case of pyrrole the Friedel-Crafts product was obtained in up to 90 % yield and up to 82 % ee.
On the Origin of Nonexponential Fluorescence Decay in Tryptophan and Its Derivatives
Petrich, J. W.,Chang, M. C.,McDonald, D. B.,Fleming, G. R.
, p. 3824 - 3832 (1983)
The nonexponential fluorescence decay of tryptophan and its derivatives is discussed in terms of a simple model based on conformers about the Cα-Cβ bond and the relative rates of charge transfer from indole to various electrophiles.Accurate predictions concerning the relative fluorescence lifetimes and the form of the fluorescence decay law are made for tryptophan and 17 of its derivatives, including three new derivatives synthesized specifically to test the model.
