Remarkably Facile Borane-Promoted, Rhodium-Catalyzed Asymmetric Hydrogenation of Tri- and Tetrasubstituted Alkenes
Autor: | James M. Takacs, Veronika M. Shoba |
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Rok vydání: | 2017 |
Předmět: |
chemistry.chemical_element
Boranes Borane Alkenes 010402 general chemistry 7. Clean energy 01 natural sciences Biochemistry Medicinal chemistry Catalysis Rhodium chemistry.chemical_compound Colloid and Surface Chemistry Molecule Organic chemistry Molecular Structure 010405 organic chemistry Chemistry Communication Asymmetric hydrogenation General Chemistry 0104 chemical sciences Hydroboration Hydrogenation Enantiomer |
Zdroj: | Journal of the American Chemical Society |
ISSN: | 1520-5126 |
Popis: | Oxime-directed catalytic asymmetric hydroboration is diverted to catalytic asymmetric hydrogenation (CAH) upon the addition of a proton source, such as MeOH, or by running the reaction under a hydrogen atmosphere. A borane (e.g., pinacolborane) is required to promote CAH. Tri- and tetrasubstituted alkenes, including the challenging all-alkyl tetrasubstituted alkenes, undergo CAH with enantiomer ratios (er) as high as 99:1. The mild reaction conditions, i.e., ambient temperature, moderate reaction times, and the need for only a slight excess of H2, contrast those used in most state-of-the-art catalysts for related substrates. |
Databáze: | OpenAIRE |
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