A fluorous cinchona alkaloid ester has been developed as a chiral promoter for the asymmetric fluorination of β-ketoesters. It has comparable reactivity and selectivity to the nonfluorous versions of cinchona alkaloids and can be easily recovered from the reaction mixture by simple fluorous solid-phase extraction (F-SPE) and used for the next round of reaction without further purification.
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http://dx.doi.org/10.3762/bjoc.8.138 | DOI Listing |
Chem Commun (Camb)
October 2021
Department of Chemistry, University of Massachusetts, 100 Morrissey Boulevard, Boston, MA 02125, USA.
Organocatalysis has unique modes of activation, mild reaction conditions, and good catalyst structural amenability. The integration of green techniques such as catalyst recovery and one-pot reactions makes organocatalysis more efficient and attractive. Presented in this article are the recyclable cinchona alkaloid-catalyzed reactions including fluorination and Michael addition-initiated cascade reactions in asymmetric synthesis of functionalized compounds of biological interest.
View Article and Find Full Text PDFJ Org Chem
July 2016
Department of Chemistry, University of Massachusetts, 100 Morrissey Boulevard, Boston, Massachusetts 02125, United States.
The first asymmetric synthesis of spiro-γ-lactam oxindoles bearing three stereocenters is reported. One-pot thiol-Michael/Mannich/lactamization reactions promoted by a recyclable fluorous bifunctional cinchona alkaloid/thiourea organocatalyst afford products in moderate to good yields with up to 95% ee and 6:1 dr.
View Article and Find Full Text PDFAnal Chim Acta
July 2015
Department of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan. Electronic address:
This paper describes the preparation of new dress-up columns featuring reproducibly removable and replaceable chiral stationary phases. After synthesizing perfluroalkylated quinine and quinidine derivatives as chiral stationary phase compounds (F-CSPs), we adsorbed them reversibly onto a fluorous LC column through pumping of their solutions. Using this dress-up chiral column and fluorophobic elution of aqueous ammonium formate/MeOH mixtures, we could enantioseparate four racemic N-acetyl amino acids, dichlorprop, and sixteen fluorescent 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC)-derivatized amino acids.
View Article and Find Full Text PDFBeilstein J Org Chem
October 2012
School of Chemical Engineering, Nanjing University of Science and Technology, Xiao Ling Wei Street, Nanjing 210094, People's Republic of China.
A fluorous cinchona alkaloid ester has been developed as a chiral promoter for the asymmetric fluorination of β-ketoesters. It has comparable reactivity and selectivity to the nonfluorous versions of cinchona alkaloids and can be easily recovered from the reaction mixture by simple fluorous solid-phase extraction (F-SPE) and used for the next round of reaction without further purification.
View Article and Find Full Text PDFTop Curr Chem
August 2012
Department of Chemistry, University of Massachusetts, Boston, MA 02125, USA.
Organocatalysis is a new and fast growing research area, especially for asymmetric synthesis. Compared to metal catalysis and biocatalysis, organocatalysis has a number of unique features such metal-free, mild reaction conditions, novel mode of activations, and good structural amenability. Fluorous organocatalysis provides an efficient way for catalyst recovery.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!