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Issue 16, 2018
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An asymmetric Mannich reaction of α-diazocarbonyl compounds and N-sulfonyl cyclic ketimines catalyzed by complexes generated from chiral and achiral phosphines with gold(I)

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Abstract

An unprecedented Lewis acidic gold(I)-complex generated from chiral and achiral phosphines has been developed for the Mannich reaction of α-diazocarbonyl compounds and N-sulfonyl cyclic ketimines. A series of chiral β-amino-α-diazoesters bearing a quaternary stereocenter were obtained in high yields with good enantioselectivities. In addition, the products could be converted to promising bioactive spirosuccinimide. Furthermore, operando IR, NMR and control experiments were carried out to gain insight into the mechanism.

Graphical abstract: An asymmetric Mannich reaction of α-diazocarbonyl compounds and N-sulfonyl cyclic ketimines catalyzed by complexes generated from chiral and achiral phosphines with gold(i)

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Publication details

The article was received on 07 Mar 2018, accepted on 23 Mar 2018 and first published on 23 Mar 2018


Article type: Paper
DOI: 10.1039/C8OB00577J
Citation: Org. Biomol. Chem., 2018,16, 2923-2931
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    An asymmetric Mannich reaction of α-diazocarbonyl compounds and N-sulfonyl cyclic ketimines catalyzed by complexes generated from chiral and achiral phosphines with gold(I)

    M. Zhou, Q. Su, Y. Addepalli, Y. He and Z. Wang, Org. Biomol. Chem., 2018, 16, 2923
    DOI: 10.1039/C8OB00577J

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