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Issue 9, 2016
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Rh-catalysed asymmetric conjugate addition of boronic acids to nitroalkenes employing a P-chiral P,π-hybrid ligand

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Abstract

A Rh-catalysed asymmetric conjugate addition of aryl boronic acids to β-substituted nitroalkenes was developed employing a P-chiral P-alkene hybrid bidentate ligand with enantioselectivities of up to 94 : 6 er. DFT modelling of the transition state for the addition reaction was consistent with our previous model for stereocontrol employing this family of chiral ligands. Application of the β-chiral nitroalkanes was demonstrated in the intramolecular Buchwald–Hartwig amination and aminocarbonylation to provide 5- and 6-membered chiral heterocycles.

Graphical abstract: Rh-catalysed asymmetric conjugate addition of boronic acids to nitroalkenes employing a P-chiral P,π-hybrid ligand

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Publication details

The article was received on 28 Jun 2016, accepted on 23 Jul 2016 and first published on 26 Jul 2016


Article type: Research Article
DOI: 10.1039/C6QO00311G
Citation: Org. Chem. Front., 2016,3, 1149-1153
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    Rh-catalysed asymmetric conjugate addition of boronic acids to nitroalkenes employing a P-chiral P,π-hybrid ligand

    J. D. Sieber, D. Rivalti, M. A. Herbage, J. T. Masters, K. R. Fandrick, D. R. Fandrick, N. Haddad, H. Lee, N. K. Yee, B. F. Gupton and C. H. Senanayake, Org. Chem. Front., 2016, 3, 1149
    DOI: 10.1039/C6QO00311G

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