Please use this identifier to cite or link to this item:
https://doi.org/10.1080/00397911.2013.791697
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 organocatalysis 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. https://doi.org/10.1080/00397911.2013.791697 | 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 | URI: | http://scholarbank.nus.edu.sg/handle/10635/76101 | ISSN: | 00397911 | DOI: | 10.1080/00397911.2013.791697 |
Appears in Collections: | Staff Publications |
Show full item record
Files in This Item:
There are no files associated with this item.
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.