Asymmetric Oxidation of Silyl Enol Ethers Using Chiral Dioxiranes derived from α-Fluoro Cyclohexanones
| Autor: | Arlette Solladié-Cavallo, Roberto Antonioletti, Paolo Bovicelli, Arlette Klein, Paolo Lupattelli, F. Angeli, Loïc Jierry |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2003 |
| Předmět: |
chemistry.chemical_classification
Ketone Silylation Organic Chemistry Absolute configuration asymmetric oxidation General Medicine fluoro cyclohexanone Biochemistry Medicinal chemistry Enol chemistry.chemical_compound chemistry Propiophenone alpha-hydroxyketone Drug Discovery dioxiranes Tetralone Organic chemistry |
| Zdroj: | Tetrahedron letters 44 (2003): 6523–6526. doi:10.1016/S0040-4039(03)01388-1 info:cnr-pdr/source/autori:Solladie-Cavallo, A.; Lupattelli, P.; Jierry, L.; Bovicelli, P.; Angeli, F.; Antonioletti, R.; Klein, A./titolo:Asymmetric oxidation of silyl enol ethers using chiral dioxiranes derived from a-fluoro cyclohexanones/doi:10.1016%2FS0040-4039(03)01388-1/rivista:Tetrahedron letters/anno:2003/pagina_da:6523/pagina_a:6526/intervallo_pagine:6523–6526/volume:44 |
| Popis: | Asymmetric oxidation of silyl enolethers derived from tetralone, 2-methyl-tetralone, propiophenone and deoxybenzoin using chiral dioxiranes generated in situ from oxone and new chiral α-fluorinated cyclohexanones or fructose-derived ketone have been studied. It was observed that tetrasubstituted silyl enolethers are poor substrates, that substitution at C8 of the fluoro-ketones has a significant effect on the enantioselectivities obtained and that the fructose-derived-ketone provides higher enantioselectivities. The absolute configuration of the major hydroxy ketones obtained can be rationalized using a spiro model proposed for epoxidation of olefins. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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