Open AccessFree Radical-Mediated Aryl Amination: Convergent Two- and Three-Component Couplings to Chiral 2,3-Disubstituted Indolines
Author(s) -
Rajesh Viswanathan,
Colin R. Smith,
Erode N. Prabhakaran,
Jeffrey N. Johnston
Publication year - 2008
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/jo702523u
Subject(s) - chemistry , amination , michael reaction , aryl , aryl radical , component (thermodynamics) , malonate , reductive amination , combinatorial chemistry , glycine , schiff base , organic chemistry , catalysis , polymer chemistry , amino acid , alkyl , physics , thermodynamics , biochemistry
5-exo-trig Cyclization of an aryl radical to the nitrogen of an azomethine is used as the key annulating step in a modular preparation of 2,3-cis- and trans-disubstituted indolines. The precursors are readily prepared by phase-transfer-catalyzed Michael addition of a glycine Schiff base to a variety of acceptors. When the more reactive alkylidene malonate Michael acceptors are implemented, a one-pot three-component coupling is possible. The net result is a convergent [3 + 2] coupling strategy for the construction of highly functionalized indolines, a substructure occurring in numerous biologically active natural products.