Asymmetric oxidation of silyl enol ethers using chiral dioxiranes derived from α-fluoro cyclohexanones |
| |
Authors: | A Solladié-Cavallo P Lupattelli L JierryP Bovicelli F AngeliR Antonioletti A Klein |
| |
Institution: | a Laboratoire de Stéréochimie Organométallique associé au CNRS, ECPM/Université L. Pasteur, 25 rue Becquerel, 67087 Strasbourg, France b Dipartimento di Chimica, Università degli studi della Basilicata, via N. Sauro 85, 85100 Potenza, Italy c CNR, Istituto di Chimica Biomolecolare, Sez. Roma c/o Dip. Chimica, Università ‘La Sapienza’, Ple A. Moro 5, Roma, Italy |
| |
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. |
| |
Keywords: | fluoro cyclohexanone dioxiranes asymmetric oxidation α-hydroxyketone |
本文献已被 ScienceDirect 等数据库收录! |
|