Asymmetric oxidation of silyl enol ethers using chiral dioxiranes derived from α-fluoro cyclohexanones
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| Title: | Asymmetric oxidation of silyl enol ethers using chiral dioxiranes derived from α-fluoro cyclohexanones |
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| Authors: | Solladié-Cavallo, A.1 cavallo@chimie.u-strasbg.fr, Lupattelli, P.1,2, Jierry, L.1, Bovicelli, P.3, Angeli, F.3, Antonioletti, R.3, Klein, A.1 |
| Source: | Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Aug2003, Vol. 44 Issue 34, p6523. 4p. |
| Subjects: | Oxidation, Ketones, Alkenes |
| Abstract: | 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. [Copyright &y& Elsevier] |
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| Database: | Engineering Source |
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