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Diastereoselective Rh-catalyzed decarboxylative allylation to form quaternary stereocenters using sulfinimine as the directing group

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Abstract

In this paper, we reported for the first time that the diastereoselective Rh-catalyzed decarboxylative allylation of chiral sulfinimines could be used to form quaternary stereocenters. The key factor in giving rise to the successful development of this method was the application of the commercially available and achiral Wilkinson's Rh catalyst. Explained by a plausible mechanism, the sulfinimine group might be a potent directing group chelated with Rh to construct intramolecular steric hindrance. In addition, broad functional group tolerance was observed, and we subsequently revealed the various transformations verifying the utility of this method for rapidly accessing complex enantio-enriched polycyclic compounds.

Graphical abstract: Diastereoselective Rh-catalyzed decarboxylative allylation to form quaternary stereocenters using sulfinimine as the directing group

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Publication details

The article was received on 21 Nov 2018, accepted on 23 Jan 2019 and first published on 24 Jan 2019


Article type: Research Article
DOI: 10.1039/C8QO01258J
Citation: Org. Chem. Front., 2019, Advance Article

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    Diastereoselective Rh-catalyzed decarboxylative allylation to form quaternary stereocenters using sulfinimine as the directing group

    S. Qin, T. Liu, Y. Luo, S. Jiang and G. Yang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01258J

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