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Cascade intramolecular N-arylation/intermolecular carboamination reactions for the construction of tricyclic heterocycles.

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.

SUBMITTER: Lemen GS

PROVIDER: S-EPMC3118464 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Cascade intramolecular N-arylation/intermolecular carboamination reactions for the construction of tricyclic heterocycles.

Lemen Georgia S GS Wolfe John P JP

Organic letters 20110523 12

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, diastereosele ...[more]

PMID: 21604733

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