Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer
| Autor: | Michael J. Krische, Ming Xiang, Leyah A. Schwartz, Kim Spielmann |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Allene
Phthalimides 010402 general chemistry Iridium 01 natural sciences Biochemistry Medicinal chemistry Article Catalysis Isotopic labeling chemistry.chemical_compound Colloid and Surface Chemistry Dehydrogenation Hydrometalation Reaction progress kinetic analysis Molecular Structure Enantioselective synthesis General Chemistry 0104 chemical sciences Alkadienes chemistry Catalytic cycle Alcohols Oxidation-Reduction Hydrogen |
| Zdroj: | J Am Chem Soc |
| Popis: | The first catalytic enantioselective carbonyl (α-amino)allylations are described. Phthalimido-allene 1 and primary alcohols 2a–2z, 2a′–2c′ engage in hydrogen auto-transfer-mediated carbonyl reductive coupling by way of (α-amino)allyliridium−aldehyde pairs to form vicinal amino alcohols 3a–3z, 3a′–3c′ with high levels of regio-, anti-diastereo-, and enantioselectivity. Reaction progress kinetic analysis and isotopic labeling studies corroborate a catalytic cycle involving turnover-limiting alcohol dehydrogenation followed by rapid allene hydrometalation. |
| Databáze: | OpenAIRE |
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