Stereospecific assembly of tetrahydroquinolines tandem ring-opening/oxidative cyclization of donor-acceptor cyclopropanes with -alkyl anilines

An aerobic copper-catalyzed tandem reaction of N -alkyl anilines with donor-acceptor cyclopropanes is presented for the construction of tetrahydroquinolines via a sequential stereospecific ring opening and oxidative cyclization. The catalyst plays a dual role as a Lewis acid as well as being a redox...

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Published inChemical communications (Cambridge, England) Vol. 55; no. 56; pp. 883 - 886
Main Authors Ketan Das, Bijay, Pradhan, Sourav, Punniyamurthy, Tharmalingam
Format Journal Article
LanguageEnglish
Published 09.07.2019
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Summary:An aerobic copper-catalyzed tandem reaction of N -alkyl anilines with donor-acceptor cyclopropanes is presented for the construction of tetrahydroquinolines via a sequential stereospecific ring opening and oxidative cyclization. The catalyst plays a dual role as a Lewis acid as well as being a redox catalyst. The use of air as an oxidant and the broad substrate scope are the important practical features. Dual role Cu-catalyzed stereospecific construction of tetrahydroquinolines has been presented with N -alkyl anilines and cyclopropanes. The use of air as an oxidant, the substrate scope and the high enantiomeric purities are the important practical features.
Bibliography:10.1039/c9cc04042k
Electronic supplementary information (ESI) available: Experimental procedure, characterization data, NMR
1
For ESI and crystallographic data in CIF or other electronic format see DOI
13
1902927
F
1902908
and
H
19
C) spectra. CCDC
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc04042k