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Org Lett. 2016 Jul 1;18(13):3294-7. doi: 10.1021/acs.orglett.6b01611. Epub 2016 Jun 23.

Convergent Synthesis of Diverse Nitrogen Heterocycles via Rh(III)-Catalyzed C-H Conjugate Addition/Cyclization Reactions.

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1
Department of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.

Abstract

The development of Rh(III)-catalyzed C-H conjugate addition/cyclization reactions that provide access to synthetically useful fused bi- and tricyclic nitrogen heterocycles is reported. A broad scope of C-H functionalization substrates and electrophilic olefin coupling partners is effective, and depending on the nature of the directing group, cyclic imide, amide, or heteroaromatic products are obtained. An efficient synthesis of a pyrrolophenanthridine alkaloid natural product, oxoassoanine, highlights the utility of this method.

PMID:
27337641
PMCID:
PMC4973575
DOI:
10.1021/acs.orglett.6b01611
[Indexed for MEDLINE]
Free PMC Article

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