Cinchona Alkaloid Squaramide/AgOAc Cooperatively Catalyzed Diastereo- and Enantioselective Mannich/Cyclization Cascade Reaction of Isocyanoacetates and Cyclic Trifluoromethyl Ketimines
| Autor: | Mei-Xin Zhao, Rong-Hui Jiang, Min Shi, Hong-Lei Bi, Xu-Wei Xu |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
Quinazoline derivatives
Trifluoromethyl Molecular Structure biology Cinchona Alkaloids Alkaloid Organic Chemistry Enantioselective synthesis Squaramide Cinchona Stereoisomerism Acetates biology.organism_classification Biochemistry Catalysis chemistry.chemical_compound Cascade reaction chemistry Cyclization Heterocyclic Compounds Nitriles Organic chemistry Imines Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 16:4566-4569 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol502123z |
| Popis: | An efficient diastereo- and enantioselective Mannich-type/cyclization cascade reaction of α-substituted isocyanoacetates and cyclic trifluoromethyl ketimines cooperatively catalyzed by cinchona alkaloid-derived multi-hydrogen-bonding donor squaramide and AgOAc has been investigated, affording the optically active trifluoromethyl-substituted tetrahydroimidazo[1,5-c]quinazoline derivatives in excellent yields (up to 99%) and good to excellent stereoselectivities (up to >15:1 dr, up to 98% ee) under mild conditions. |
| Databáze: | OpenAIRE |
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