C–H Functionalization of Amines via Alkene-Derived Nucleophiles through Cooperative Action of Chiral and Achiral Lewis Acid Catalysts: Applications in Enantioselective Synthesis
| Autor: | Yejin Chang, Jessica Z. Chan, Ming Shang, Masayuki Wasa, Qifan Wang, Min Cao, Sebastian Torker, Brennan Cook |
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| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Chemistry Alkene Enantioselective synthesis Stereoisomerism General Chemistry Alkenes 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Article Catalysis 0104 chemical sciences Colloid and Surface Chemistry Nucleophile Atom economy Electrophile Lewis acids and bases Amines Oxidation-Reduction Lewis Acids |
| Popis: | Catalytic transformations of α-amino C–H bonds to afford valuable enantiomerically enriched α-substituted amines, entities that are prevalent in pharmaceuticals and bioactive natural products, have been developed. Typically, such processes are carried out under oxidative conditions, and require precious metal-based catalysts. Here, we disclose a strategy for enantioselective union of N-alkylamines and α,β-unsaturated compounds, performed under redox-neutral conditions, and promoted through concerted action of seemingly competitive Lewis acids, B(C(6)F(5))(3) and a chiral Mg–PyBOX complex. Thus, a wide variety of β-amino carbonyl compounds may be synthesized, with complete atom economy, through stereoselective reaction of an in situ generated enantiomerically enriched Mg-enolate and an appropriate electrophile. |
| Databáze: | OpenAIRE |
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