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Angew Chem Int Ed Engl. 2013 Jan 7;52(2):629-33. doi: 10.1002/anie.201207995. Epub 2012 Nov 22.

Rhodium(III)-catalyzed alkenyl C-H bond functionalization: convergent synthesis of furans and pyrroles.

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  • 1Department of Chemistry, Yale University, New Haven, CT 06520, USA.

Abstract

Ring in the new: a new annulation for the efficient synthesis of substituted furans and pyrroles is reported. The Rh(III) -catalyzed reaction of O-methyl α,β-unsaturated oximes with aldehydes and N-tosyl imines affords secondary alcohol and amine intermediates, respectively. Cyclization and aromatization occurs under the reaction conditions to provide access to biologically relevant furans and pyrroles in good yields. Cp*=C(5)Me(5), DCE=1,2-dichloroethane, THF=tetrahydrofuran.

Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PMID:
23172703
[PubMed - indexed for MEDLINE]
PMCID:
PMC3770945
Free PMC Article
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