Please use this identifier to cite or link to this item: https://doi.org/10.1002/asia.201300141
Title: Molecular assembly of an achiral phosphine and a chiral primary amine: A highly efficient supramolecular catalyst for the enantioselective michael reaction of aldehydes with maleimides
Authors: Yang, W.
Jiang, K.-Z.
Lu, X.
Yang, H.-M.
Li, L.
Lu, Y. 
Xu, L.-W.
Keywords: aldehydes
Michael addition
molecular assembly
organocatalysis
supramolecular chemistry
Issue Date: Jun-2013
Citation: Yang, W., Jiang, K.-Z., Lu, X., Yang, H.-M., Li, L., Lu, Y., Xu, L.-W. (2013-06). Molecular assembly of an achiral phosphine and a chiral primary amine: A highly efficient supramolecular catalyst for the enantioselective michael reaction of aldehydes with maleimides. Chemistry - An Asian Journal 8 (6) : 1182-1190. ScholarBank@NUS Repository. https://doi.org/10.1002/asia.201300141
Abstract: A combined catalyst system of a cinchonidine-derived primary amine and triphenylphosphine (CD-NH2/PPh3) exhibited high catalytic performance in the Michael reaction of aldehydes with maleimides, thereby affording the corresponding functionalized aldehydes in excellent yields (up to 99 %) and enantioselectivities (>99 % ee). More interestingly, the significance of the phosphine in enhancing the enantioselectivities in the chiral-primary-amine-catalyzed Michael reaction was revealed. Furthermore, we explored the origin of the reaction mechanism in the Michael addition promoted by the dual organocatalytic system. On the basis of experimental results and spectroscopic analysis, such as UV/Vis, fluorescence emission (FL), NMR, and circular dichroism (CD) spectroscopy, as well as ES-MS, we found that the molecular assembly of phosphine and primary amine played a crucial role in this enantioselective reaction, in which a possible supramolecular complex was formed as an effective chiral catalyst through noncovalent molecular interactions of a cinchona alkaloid-derived primary amine with triphenylphosphine. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Source Title: Chemistry - An Asian Journal
URI: http://scholarbank.nus.edu.sg/handle/10635/94300
ISSN: 18614728
DOI: 10.1002/asia.201300141
Appears in Collections:Staff Publications

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