Redox-Triggered C–C Coupling of Alcohols and Vinyl Epoxides: Diastereo- and Enantioselective Formation of All-Carbon Quaternary Centers via tert-(Hydroxy)-Prenylation
| Autor: | Victoria J. Garza, Michael J. Krische, Jiajie Feng |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
Vinyl Compounds
Stereochemistry chemistry.chemical_element Stereoisomerism Primary alcohol Iridium Biochemistry Redox Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Bond cleavage Isoprene Prenylation Molecular Structure Terpenes Communication Enantioselective synthesis General Chemistry chemistry Alcohols Epoxy Compounds Oxidation-Reduction |
| Zdroj: | Journal of the American Chemical Society |
| ISSN: | 1520-5126 0002-7863 |
| Popis: | Iridium catalyzed primary alcohol oxidation triggers reductive C–O bond cleavage of isoprene oxide to form aldehyde-allyliridium pairs that combine to form products of tert-(hydroxy)-prenylation, a motif found in >2000 terpenoid natural products. Curtin–Hammett effects are exploited to enforce high levels of anti-diastereo- and enantioselectivity in the formation of an all-carbon quaternary center. The present redox-triggered carbonyl additions occur in the absence of stoichiometric byproducts, premetalated reagents, and discrete alcohol-to-aldehyde redox manipulations. |
| Databáze: | OpenAIRE |
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