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Issue 9, 2016

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

Supplementary files

Article information


Submitted
28 Jun 2016
Accepted
23 Jul 2016
First published
26 Jul 2016

Org. Chem. Front., 2016,3, 1149-1153
Article type
Research Article

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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