Free Radical-Mediated Aryl Amination: Convergent Two- and Three-Component Couplings to Chiral 2,3-Disubstituted Indolines | Zendy

Rajesh Viswanathan | Zendy; Colin R. Smith | Zendy; Erode N. Prabhakaran | Zendy; Jeffrey N. Johnston | Zendy

Open Access

Free 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 -

the 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 , aryl , aryl radical , michael reaction , malonate , component (thermodynamics) , amination , reductive amination , schiff base , combinatorial chemistry , glycine , organic chemistry , catalysis , stereochemistry , amino acid , biochemistry , alkyl , physics , thermodynamics

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.

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