title: Free radical-mediated aryl amination: convergent two- and three-component couplings to chiral 2,3-disubstituted indolines.
abstract: 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.
authors: Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA.
authors: Rajesh
authors: R
authors: Viswanathan
authors: Colin R
authors: CR
authors: Smith
authors: Erode N
authors: EN
authors: Prabhakaran
authors: Jeffrey N
authors: JN
authors: Johnston
mesh_terms: D000478:Alkylation; D000586:Amination; D001372:Aza Compounds / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; D004952:Esters; D005609:Free Radicals; D007211:Indoles; C057812:indoline