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Issue 7, 2017
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Squaramide-catalyzed domino Michael/aza-Henry [3 + 2] cycloaddition: asymmetric synthesis of functionalized 5-trifluoromethyl and 3-nitro substituted pyrrolidines

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Abstract

The diastereo- and enantioselective Michael/aza-Henry [3 + 2] cycloaddition reaction of trifluoromethyl-substituted iminomalonate and nitroalkenes has been developed employing 10 mol% of a quinine-squaramide catalyst. A series of highly functionlized 5-trifluoromethyl and 3-nitro substituted pyrrolidine derivatives containing three contiguous stereogenic centers are efficiently prepared with very good yields and excellent stereoselectivities (up to 82% yield, >20 : 1 dr, and 99% ee).

Graphical abstract: Squaramide-catalyzed domino Michael/aza-Henry [3 + 2] cycloaddition: asymmetric synthesis of functionalized 5-trifluoromethyl and 3-nitro substituted pyrrolidines

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Publication details

The article was received on 27 Feb 2017, accepted on 19 Apr 2017 and first published on 24 Apr 2017


Article type: Research Article
DOI: 10.1039/C7QO00161D
Citation: Org. Chem. Front., 2017,4, 1416-1419
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    Squaramide-catalyzed domino Michael/aza-Henry [3 + 2] cycloaddition: asymmetric synthesis of functionalized 5-trifluoromethyl and 3-nitro substituted pyrrolidines

    Q. Liu, K. Zhao, Y. Zhi, G. Raabe and D. Enders, Org. Chem. Front., 2017, 4, 1416
    DOI: 10.1039/C7QO00161D

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