Enantioselective Heck arylations of acyclic alkenyl alcohols using a redox-relay strategy
| Autor: | Tian-Sheng Mei, Matthew S. Sigman, Erik W. Werner, Alexander J. Burckle |
|---|---|
| Rok vydání: | 2012 |
| Předmět: |
chemistry.chemical_classification
Multidisciplinary Ketone Chemistry Alkene Migratory insertion Enantioselective synthesis Regioselectivity Stereoisomerism Chemistry Techniques Synthetic Diazonium Compounds Alkenes Ketones Catalysis Chain walking Alcohols Organic chemistry Selectivity Oxidation-Reduction |
| Zdroj: | Science (New York, N.Y.). 338(6113) |
| ISSN: | 1095-9203 |
| Popis: | From C=C to C=O The palladium-catalyzed Heck reaction is widely used to form carbon-carbon bonds between aryl rings and olefins, after which elimination of a hydrogen atom restores the olefin's double bond. Werner et al. (p. 1455 ; see the Perspective by Gilbertson ) present a variant of this reaction in which a hydrogen atom is instead lost from an alcohol center elsewhere in the molecule, yielding a ketone and a chiral center where the arene is bound. The process is highly enantioselective and also versatile: The alcohol can be sited one, two, or even three carbons away from the olefin. |
| Databáze: | OpenAIRE |
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