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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Cascade intramolecular N-arylation/intermolecular carboamination reactions for the construction of tricyclic
Georgia S Lemen1, John P Wolfe
1Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan, 48109-1055, USA.
Abstract:
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.
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