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

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    Letter

    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
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    Organic Letters

    Cite this: Org. Lett. 2006, 8, 18, 3895–3898
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    https://doi.org/10.1021/ol0612197
    Published August 8, 2006
    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.

    Copyright © 2006 American Chemical Society

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    †

     ICIQ.

    ‡

     ICIQ and ICREA.

    *

    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

    §

     ICIQ and UB.

    Supporting Information Available

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    Experimental procedures and characterization of 1a−c. 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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    Cited By

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    This article is cited by 12 publications.

    1. Pablo Etayo, José L. Núñez-Rico, and Anton Vidal-Ferran . Chiral Rhodium Complexes Derived From Electron-Rich Phosphine-Phosphites as Asymmetric Hydrogenation Catalysts. Organometallics 2011, 30 (24) , 6718-6725. https://doi.org/10.1021/om200933b
    2. José L. Núñez-Rico, Héctor Fernández-Pérez, J. Benet-Buchholz, and Anton Vidal-Ferran . Asymmetric Hydrogenation of Heteroaromatic Compounds Mediated by Iridium−(P-OP) Complexes. Organometallics 2010, 29 (24) , 6627-6631. https://doi.org/10.1021/om100955t
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    4. F. Faigl, SZ. Deák, ZS. Erdélyi, T. Holczbauer, M. Czugler, M. Nyerges, B. Mátravölgyi. New Atropisomeric Amino Alcohol Ligands for Enantioselective Addition of Diethylzinc to Aldehydes. Chirality 2015, 27 (3) , 216-222. https://doi.org/10.1002/chir.22415
    5. Ciril Jimeno, Ute Christmann, Eduardo C. Escudero‐Adán, Ramon Vilar, Miquel A. Pericàs . Studies on the Amination of Aryl Chlorides with a Monoligated Palladium Catalyst: Kinetic Evidence for a Cooperative Mechanism. Chemistry – A European Journal 2012, 18 (51) , 16510-16516. https://doi.org/10.1002/chem.201202140
    6. José L. Núñez‐Rico, Pablo Etayo, Héctor Fernández‐Pérez, Anton Vidal‐Ferran. Modular POP Ligands in Rhodium‐Mediated Asymmetric Hydrogenation: A Comparative Catalysis Study. Advanced Synthesis & Catalysis 2012, 354 (16) , 3025-3035. https://doi.org/10.1002/adsc.201200477
    7. Xisco Caldentey, Xacobe C. Cambeiro, Miquel A. Pericàs. Modular optimization of enantiopure epoxide-derived P,S-ligands for rhodium-catalyzed hydrogenation of dehydroamino acids. Tetrahedron 2011, 67 (23) , 4161-4168. https://doi.org/10.1016/j.tet.2011.04.050
    8. Armen Panossian, Héctor Fernández-Pérez, Dana Popa, Anton Vidal-Ferran. Highly modular P-OP ligands in asymmetric allylic substitution. Tetrahedron: Asymmetry 2010, 21 (18) , 2281-2288. https://doi.org/10.1016/j.tetasy.2010.08.004
    9. Héctor Fernández‐Pérez, Steven M. A. Donald, Ian J. Munslow, Jordi Benet‐Buchholz, Feliu Maseras, Anton Vidal‐Ferran. Highly Modular POP Ligands for Asymmetric Hydrogenation: Synthesis, Catalytic Activity, and Mechanism. Chemistry – A European Journal 2010, 16 (22) , 6495-6508. https://doi.org/10.1002/chem.200902915
    10. Sílvia Subirats, Ciril Jimeno, Miquel A. Pericàs. Amino thiols versus amino alcohols in the asymmetric alkynylzinc addition to aldehydes. Tetrahedron: Asymmetry 2009, 20 (12) , 1413-1418. https://doi.org/10.1016/j.tetasy.2009.05.029
    11. Dina Scarpi, Ernesto G. Occhiato, Antonio Guarna. N-Substituent effects on the diethylzinc addition to benzaldehyde catalysed by bicyclic 1,4-amino alcohols. Tetrahedron: Asymmetry 2009, 20 (3) , 340-350. https://doi.org/10.1016/j.tetasy.2009.01.021
    12. Héctor Fernández‐Pérez, Miquel A. Pericàs, Anton Vidal‐Ferran. Highly Modular P‐O‐P Ligands for Asymmetric Hydrogenation. Advanced Synthesis & Catalysis 2008, 350 (13) , 1984-1990. https://doi.org/10.1002/adsc.200800311
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    Organic Letters

    Cite this: Org. Lett. 2006, 8, 18, 3895–3898
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol0612197
    Published August 8, 2006
    Copyright © 2006 American Chemical Society
    Request reuse permissions

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