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Enantioselective Copper(II)/Box‐Catalyzed Synthesis of Chiral β 3 ‐Tryptophan Derivatives
Author(s) -
Tarasenko Elena A.,
Shestakov Ivan V.,
Rybakov Victor B.,
Beletskaya Irina P.
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201900575
Subject(s) - enantioselective synthesis , friedel–crafts reaction , chemistry , pyrrole , catalysis , yield (engineering) , alkylation , organic chemistry , tryptophan , copper , combinatorial chemistry , amino acid , materials science , biochemistry , metallurgy
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 β 3 ‐tryptophan derivatives based on enantioselective Friedel‐Crafts alkylation of indoles with phthaloyl‐protected aminomethylenemalonate in the presence of chiral Cu OTf 2 / i PrBox 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 .