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Issue 8, 2018
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Diastereo- and enantioselective additions of α-nitro esters to imines for anti-α,β-diamino acid synthesis with α-alkyl-substitution

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Abstract

The discovery that a C2-symmetric bis(AMidine) [BAM] catalyst promotes an anti-selective addition of α-substituted α-nitro esters to imines is described, providing α-substituted α,β-diamino ester products with high diastereo- and enantioselectivity. When compared to the function of a BAM catalyst reported previously, the pair offer a rare example of diastereodivergence using a bifunctional Brønsted acid–base organocatalyst.

Graphical abstract: Diastereo- and enantioselective additions of α-nitro esters to imines for anti-α,β-diamino acid synthesis with α-alkyl-substitution

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Publication details

The article was received on 05 Dec 2017, accepted on 23 Jan 2018 and first published on 31 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC05176J
Citation: Chem. Sci., 2018,9, 2336-2339
  • Open access: Creative Commons BY license
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    Diastereo- and enantioselective additions of α-nitro esters to imines for anti-α,β-diamino acid synthesis with α-alkyl-substitution

    D. J. Sprague, A. Singh and J. N. Johnston, Chem. Sci., 2018, 9, 2336
    DOI: 10.1039/C7SC05176J

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