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Pyrrolidine aminal skeletons are found in many natural products and biologically active compounds. Therefore, the development of a new methodology for rapid access to this core is of high importance. Herein, we first reported results of a Pd(0)-catalyzed three-component hydroamidation/Heck/Tsuji-Trost reaction to afford fluorinated 3-pyrroline aminal derivatives based on β-CF-1,3-enynamides.
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http://dx.doi.org/10.1021/acs.joc.5c01479 | DOI Listing |
J Org Chem
August 2025
School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Rd., Shanghai 200241, P. R. China.
Pyrrolidine aminal skeletons are found in many natural products and biologically active compounds. Therefore, the development of a new methodology for rapid access to this core is of high importance. Herein, we first reported results of a Pd(0)-catalyzed three-component hydroamidation/Heck/Tsuji-Trost reaction to afford fluorinated 3-pyrroline aminal derivatives based on β-CF-1,3-enynamides.
View Article and Find Full Text PDFJ Org Chem
December 2012
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom.
The presence of fluorous substituents can impart a dramatic effect on the efficacy of molecules used for a range of applications in society. Here, we describe the preparation and use of a new trifluoromethylated azomethine ylide precursor, which leads to a series of fluorinated pyrrolidine, 3-pyrroline, and pyrrole building blocks.
View Article and Find Full Text PDFJ Org Chem
February 2005
Chemistry Institute, State University of Campinas-UNICAMP, 13084-971, Campinas, São Paulo, Brazil.
We report herein a new, practical, and economic synthesis of the phosphodiesterase inhibitor Rolipram on a multigram scale as well as the synthesis of new 4-aryl pyrrolidones and beta-aryl-gamma-amino butyric acids (GABA derivatives) employing an efficient Heck-Matsuda arylation of 3-pyrroline with aryldiazonium tetrafluoroborates. Racemic Rolipram was resolved into its enantiomers using chiral simulated moving bed chromatography having the low-cost microcrystalline cellulose triacetate as a chiral stationary phase.
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