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Title: Enantioselective fluorination reaction of β-Ketoester-catalyzed chiral primary amine-based multifunctional catalyst systems
Authors: Shang, J.-Y.
Li, L.
Lu, Y. 
Yang, K.-F.
Xu, L.-W.
Keywords: Amino acid
enantioselective fluorination
Lewis acid
primary amine
Issue Date: 2-Jan-2014
Citation: Shang, J.-Y., Li, L., Lu, Y., Yang, K.-F., Xu, L.-W. (2014-01-02). Enantioselective fluorination reaction of β-Ketoester-catalyzed chiral primary amine-based multifunctional catalyst systems. Synthetic Communications 44 (1) : 101-114. ScholarBank@NUS Repository.
Abstract: The fluorination reaction is an important organic transformation for asymmetric synthesis. In this article, we reported the determination of chiral primary amine-based multicatalyst systems for enantioselective fluorination of β-ketoester. Studies on the enantioselective organocatalytic fluorination promoted by cinchona alkaloid-derived chiral primary amines in the absence of various co catalysts revealed that the combined metal salts and organocatalysts resulted in poor conversion and enantioselectivities, whereas the combinational use of L-leucine and QN-NH2 as dual primary amine catalysts led to the determination of a novel dual organocatalyst with promising catalytic activity. On the basis of these results, we revealed that the steric environment of the chiral enamine intermediate formed by the condensation of β-ketoester with the chiral primary amine is most responsible for the observed enantioselectivity. © Taylor and Francis Group, LLC.
Source Title: Synthetic Communications
ISSN: 00397911
DOI: 10.1080/00397911.2013.791697
Appears in Collections:Staff Publications

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