Sequential Allylic C–H Amination/Vinylic C–H Arylation: A Strategy for Unnatural Amino Acid Synthesis from α-Olefins
| Autor: | M. Christina White, Dustin J. Covell, Mark S. Plummer, Chao Jiang, Antonia F. Stepan |
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| Rok vydání: | 2012 |
| Předmět: |
chemistry.chemical_classification
Allylic rearrangement Molecular Structure Aryl Organic Chemistry Stereoisomerism Alkenes Biochemistry Article Catalysis Amino acid chemistry.chemical_compound Enantiopure drug Cascade reaction chemistry Organic chemistry Amino Acids Physical and Theoretical Chemistry Amination |
| Zdroj: | Organic Letters. 14:1386-1389 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | Tandem reaction sequences that selectively convert multiple C-H bonds of abundant hydrocarbon feedstocks to functionalized materials enable rapid buildup of molecular complexity in an economical way. A tandem C-H amination/vinylic C-H arylation reaction sequence is described under Pd(II)/sulfoxide-catalysis that furnishes a wide range of α- and β-homophenylalanine precursors from commodity α-olefins and readily available aryl boronic acids. General routes to enantiopure amino acid esters and densely functionalized homophenylalanine derivatives are demonstrated. |
| Databáze: | OpenAIRE |
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