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Issue 2, 2015
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Asymmetric Lewis acid catalysis directed by octahedral rhodium centrochirality

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Abstract

A rhodium-based asymmetric catalyst is introduced which derives its optical activity from octahedral centrochirality. Besides providing the exclusive source of chirality, the rhodium center serves as a Lewis acid by activating 2-acyl imidazoles through two point binding and enabling a very effective asymmetric induction mediated by the propeller-like C2-symmetrical ligand sphere. Applications to asymmetric Michael additions (electrophile activation) as well as asymmetric α-aminations (nucleophile activation) are disclosed, for which the rhodium catalyst is found to be overall superior to its iridium congener. Due to its straightforward proline-mediated synthesis, high catalytic activity (catalyst loadings down to 0.1 mol%), and tolerance towards moisture and air, this novel class of chiral-at-rhodium catalysts will likely to become of widespread use as chiral Lewis acid catalysts for a large variety of asymmetric transformations.

Graphical abstract: Asymmetric Lewis acid catalysis directed by octahedral rhodium centrochirality

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Publication details

The article was received on 09 Oct 2014, accepted on 07 Nov 2014 and first published on 10 Nov 2014


Article type: Edge Article
DOI: 10.1039/C4SC03101F
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Chem. Sci., 2015,6, 1094-1100
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    Asymmetric Lewis acid catalysis directed by octahedral rhodium centrochirality

    C. Wang, L. Chen, H. Huo, X. Shen, K. Harms, L. Gong and E. Meggers, Chem. Sci., 2015, 6, 1094
    DOI: 10.1039/C4SC03101F

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