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Ligand Anatomy:  Probing Remote Substituent Effects in Asymmetric Catalysis through NMR and Kinetic Analysis

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Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans, 16, 43007 Tarragona, Spain, Departament de Química Orgànica, Universitat de Barcelona (UB), 08028 Barcelona, Spain, and ICREA
Cite this: Org. Lett. 2006, 8, 18, 3895–3898
Publication Date (Web):August 8, 2006
https://doi.org/10.1021/ol0612197
Copyright © 2006 American Chemical Society

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    Abstract

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    A series of structurally related β-amino alcohols only differing in the steric bulk of a remote alkoxy group exhibit striking differences in kinetic behavior when used as ligands in the asymmetric diethylzinc addition to benzaldehyde (R = Trityl, much more active). A combination of NMR titration studies and kinetic analysis allows the quantitative decomposition of the remote substituent effect into a lower dimerization constant of the active species and a much faster ethyl addition step.

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     ICIQ.

     ICIQ and ICREA.

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     ICIQ and UB.

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    Experimental procedures and characterization of 1ac. Plots of concentration vs time and product inhibition. Measurement of dimerization constants by NMR. This material is available free of charge via the Internet at http://pubs.acs.org.

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