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Enantioselective aza-Henry reaction of t-Boc protected imines and nitroalkanes with bifunctional squaramide organocatalysts

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Abstract

An organocatalytic asymmetric aza-Henry reaction of t-Boc protected imines with nitroalkanes has been established by chiral acid–base type bifunctional Cinchona alkaloid/squaramide organocatalysts. The cooperation of a quinine motif as a base and sterically encumbered squaramide (H-bond donor) enabled mostly complete conversion of a range of reactants into the corresponding aza-Henry products at room temperature with good selectivities (up to 91% ee with 10 mol% catalyst loading).

Graphical abstract: Enantioselective aza-Henry reaction of t-Boc protected imines and nitroalkanes with bifunctional squaramide organocatalysts

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Publication details

The article was received on 26 Dec 2016, accepted on 30 Mar 2017 and first published on 03 Apr 2017


Article type: Paper
DOI: 10.1039/C6NJ04078K
Citation: New J. Chem., 2017, Advance Article
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    Enantioselective aza-Henry reaction of t-Boc protected imines and nitroalkanes with bifunctional squaramide organocatalysts

    D. Susam and C. Tanyeli, New J. Chem., 2017, Advance Article , DOI: 10.1039/C6NJ04078K

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