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Issue 35, 2015
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Strategy of total synthesis based on the use of Rh-catalyzed stereoselective 1,4-addition

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Abstract

In 1998, Hayashi and Miyaura reported the first asymmetric conjugate addition of aryl- and alkenyl-boronic acids to α,β-unsaturated ketones using chiral rhodium complexes as catalysts. During the last decade, this reaction has been developed quickly and the enantioselectivity was significantly improved with the emergence of new phosphine ligands. In addition to the methodological work, this reaction was applied as a key step in the total synthesis of natural compounds. The purpose of this paper focuses on examples of the use of this reaction to prepare elaborated chiral molecules with high diastereoselectivies and/or enantioselectivities.

Graphical abstract: Strategy of total synthesis based on the use of Rh-catalyzed stereoselective 1,4-addition

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Publication details

The article was received on 10 Jul 2015, accepted on 30 Jul 2015 and first published on 30 Jul 2015


Article type: Review Article
DOI: 10.1039/C5OB01402F
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 9168-9175
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    Strategy of total synthesis based on the use of Rh-catalyzed stereoselective 1,4-addition

    M. Jean, B. Casanova, S. Gnoatto and P. van de Weghe, Org. Biomol. Chem., 2015, 13, 9168
    DOI: 10.1039/C5OB01402F

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