American Chemical Society
ol201123b_si_002.pdf (4.53 MB)

Cascade Intramolecular N-Arylation/Intermolecular Carboamination Reactions for the Construction of Tricyclic Heterocycles

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journal contribution
posted on 2011-06-17, 00:00 authored by Georgia S. Lemen, John P. Wolfe
A new method for the stereoselective synthesis of tetrahydropyrroloindoles and hexahydropyrroloquinolines of general structure 8 is described. These products are formed through cascade Pd-catalyzed coupling reactions between aryl chlorides and unsaturated amine substrates 5. A single catalyst effects an intramolecular N-arylation reaction followed by an intermolecular alkene carboamination reaction to generate two rings, three bonds, and one stereocenter with good chemoselectivity, diastereoselectivity, and chemical yield.