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Issue 5, 2017
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Chiral bidentate [N,S]-ferrocene ligands based on a thiazoline framework. Synthesis and use in palladium-catalyzed asymmetric allylic alkylation

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Abstract

An efficient method to obtain chiral 1,2-disubstituted ferrocenyl ligands has been developed. The introduction of planar chirality was accomplished by using 2-thiazoline as an ortho-directing lithiation group, and moreover, these kinds of ligands possess a central chirality from the amino alcohol used in their synthesis. The X-ray analysis and DFT calculations confirmed the diastereoselectivity of ortho-lithiation and the configuration of the planar chirality. The ability of these new bidentate [N,S]-ferrocene ligands to act in Pd-catalyzed asymmetric allylic alkylation has also been demonstrated and compared with their oxazoline counterparts.

Graphical abstract: Chiral bidentate [N,S]-ferrocene ligands based on a thiazoline framework. Synthesis and use in palladium-catalyzed asymmetric allylic alkylation

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Publication details

The article was received on 26 Oct 2016, accepted on 31 Dec 2016 and first published on 02 Jan 2017


Article type: Paper
DOI: 10.1039/C6DT04119A
Citation: Dalton Trans., 2017,46, 1510-1519
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    Chiral bidentate [N,S]-ferrocene ligands based on a thiazoline framework. Synthesis and use in palladium-catalyzed asymmetric allylic alkylation

    E. P. Sánchez-Rodríguez, F. Hochberger-Roa, R. Corona-Sánchez, J. E. Barquera-Lozada, R. A. Toscano, M. Urrutigoïty, M. Gouygou, M. C. Ortega-Alfaro and J. G. López-Cortés, Dalton Trans., 2017, 46, 1510
    DOI: 10.1039/C6DT04119A

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