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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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Supplementary files

Article information


Submitted
09 Oct 2014
Accepted
07 Nov 2014
First published
10 Nov 2014

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 1094-1100
Article type
Edge Article
Author version available

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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