Ruthenium-BINAP Catalyzed Alcohol C–H tert-Prenylation via 1,3-Enyne Transfer Hydrogenation: Beyond Stoichiometric Carbanions in Enantioselective Carbonyl Propargylation
| Autor: | Khoa D. Nguyen, Michael J. Krische, Daniel Herkommer |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_element
Alcohol Naphthalenes 010402 general chemistry Transfer hydrogenation 01 natural sciences Biochemistry Medicinal chemistry Ruthenium Article Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Organic chemistry Carbanion BINAP Prenylation Enyne 010405 organic chemistry Enantioselective synthesis Stereoisomerism General Chemistry 0104 chemical sciences chemistry Alcohols Alkynes Indicators and Reagents Hydrogenation |
| Zdroj: | Journal of the American Chemical Society. 138:5238-5241 |
| ISSN: | 1520-5126 0002-7863 |
| Popis: | The chiral ruthenium complex formed in situ from (TFA)2Ru(CO)(PPh3)2 and (R)-BINAP is found to catalyze the enantioselective C-C coupling of diverse primary alcohols with the 1,3-enyne, TMSC≡CC(Me)=CH2, to form secondary homopropargyl alcohols bearing gem-dimethyl groups. All reagents for this byproduct-free coupling are inexpensive and commercially available, making this protocol a practical alternative to stoichiometric carbanions in enantioselective carbonyl reverse prenylation. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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