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Catalytic Reductive Synthesis and Direct Derivatization of Unprotected Aminoindoles, Aminopyrroles, and Iminoindolines
Author(s) -
Leijendekker Leonardus H.,
Weweler Jens,
Leuther Tobias M.,
Streuff Jan
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201702310
Subject(s) - derivatization , combinatorial chemistry , catalysis , substrate (aquarium) , chemistry , hazardous waste , protecting group , organic chemistry , waste management , engineering , high performance liquid chromatography , oceanography , geology , alkyl
Abstract A titanium(III)‐catalyzed radical cyclization to unprotected 3‐aminoindoles, 3‐aminopyrroles, or 3‐iminoindolines is reported. The reaction is non‐hazardous, scalable, and allows facile isolation of the free products by extraction. The method is demonstrated on a large substrate scope and it further allows the direct installation of various nitrogen protecting groups or the synthesis of building blocks for peptide chemistry in a single sequence. Fused bisindoles can be directly accessed from the cyclization products.