Free radical-mediated aryl amination: convergent two- and three-component couplings to chiral 2,3-disubstituted indolines |
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| Authors: | Viswanathan Rajesh Smith Colin R Prabhakaran Erode N Johnston Jeffrey N |
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| Institution: | Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA. |
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| 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. |
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