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Organocatalytic regioselective, diastereoselective, and enantioselective annulation of cyclic 1-azadienes with γ-nitro ketones via 3,4-cyclization

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Abstract

A regio-, diastereo-, and enantioselective [2 + 4] annulation reaction of cyclic 1-azadienes with γ-nitro ketones is reported. In the presence of a chiral tertiary amine, the annulation reaction proceeded smoothly to furnish polysubstituted cyclohexanes in 43–95% yields with 80–98% ee via 3,4-addition. Notably, four consecutive stereocenters including one tetrasubstituted carbon stereocentre could be constructed in one-pot via this methodology.

Graphical abstract: Organocatalytic regioselective, diastereoselective, and enantioselective annulation of cyclic 1-azadienes with γ-nitro ketones via 3,4-cyclization

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Publication details

The article was received on 20 Dec 2016, accepted on 31 Mar 2017 and first published on 05 Apr 2017


Article type: Research Article
DOI: 10.1039/C6QO00832A
Citation: Org. Chem. Front., 2017, Advance Article
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    Organocatalytic regioselective, diastereoselective, and enantioselective annulation of cyclic 1-azadienes with γ-nitro ketones via 3,4-cyclization

    L. Yu, Y. Cheng, F. Qi, R. Li and P. Li, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C6QO00832A

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