Literature DB >> 34964164

Enantioselective synthesis and selective functionalization of 4-aminotetrahydroquinolines as novel GLP-1 secretagogues.

Mustafa Z Kazancioglu1,2, Kevin Quirion1, Peter Wipf1,3, Erin M Skoda1,4.   

Abstract

Polysubstituted tetrahydroquinolines were obtained in moderate to high yields (28% to 92%) and enantiomeric ratios (er 89:11 to 99:1) by a three-component Povarov reaction using a chiral phosphoric acid catalyst. Significantly, post-Povarov functional group interconversions allowed a rapid access to a library of 36 enantioenriched 4-aminotetrahydroquinoline derivatives featuring five points of diversity. Selected analogs were assayed for their ability to function as glucagon-like peptide-1 (GLP-1) secretagogues.
© 2021 Wiley Periodicals LLC.

Entities:  

Keywords:  4-aminotetrahydroquinoline; GLP-1 secretagogues; Povarov reaction; asymmetric catalysis; chiral phosphoric acid; diversity-oriented synthesis

Mesh：

Substances：

Year:  2021        PMID： 34964164      PMCID： PMC8837726          DOI： 10.1002/chir.23403

Source DB:  PubMed          Journal:  Chirality        ISSN： 0899-0042            Impact factor:   2.437


  18 in total

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