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Issue 87, 2015
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Dual metal and Lewis base catalysis approach for asymmetric synthesis of dihydroquinolines and the α-arylation of aldehydes via N-acyliminium ions

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Abstract

A dual catalytic system consisting of indium triflate and a chiral imidazolidinone catalyzes the asymmetric addition of aldehydes to N-acyl quinoliniums furnishing optically active dihydroquinolines in good yields and excellent selectivities. The products were further functionalized into optically active tetrahydroquinolines, quinolines and 6-oxa-2-aza-bicyclo[3.3.1]nonanes.

Graphical abstract: Dual metal and Lewis base catalysis approach for asymmetric synthesis of dihydroquinolines and the α-arylation of aldehydes via N-acyliminium ions

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Article information


Submitted
24 Jun 2015
Accepted
31 Aug 2015
First published
14 Sep 2015

Chem. Commun., 2015,51, 15788-15791
Article type
Communication

Dual metal and Lewis base catalysis approach for asymmetric synthesis of dihydroquinolines and the α-arylation of aldehydes via N-acyliminium ions

C. M. R. Volla, E. Fava, I. Atodiresei and M. Rueping, Chem. Commun., 2015, 51, 15788
DOI: 10.1039/C5CC05209B

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