Kinetic resolution of acyclic secondary allylic silyl ethers by chiral dioxiranes generated in situ from chiral ketones (R)-1 and (R)-2 and Oxone was investigated. An efficient and catalytic method has been developed for kinetic resolution of those substrates with a CCl(3), tert-butyl, or CF(3) group at the alpha-position. In particular, high selectivities (S up to 100) were observed for kinetic resolutions of racemic alpha-trichloromethyl allylic silyl ethers 7 and 9-15 catalyzed by ketones (R)-2. Both the recovered substrates and the resulting epoxides were obtained in high enantiomeric excess. On the basis of steric and electrostatic interactions between the chiral dioxiranes and the racemic substrates, a model was proposed to rationalize the enantioselectivities and diastereoselectivities in the chiral ketone-catalyzed kinetic resolution process.
The Journal of organic chemistry. 2001 Jun 29;66(13):4619-24. doi: 10.1021/jo010068c Q13.62025
Kinetic resolution of acyclic secondary allylic silyl ethers catalyzed by chiral ketones
手性酮催化的非环二级烯丙基硅醚的动力学拆分 翻译改进
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DOI: 10.1021/jo010068c PMID: 11421782
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