Abstract
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 CCl3, tert-butyl, or CF3group at the α-position. In particular, high selectivities (S up to 100) were observed for kinetic resolutions of racemic α-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.
Original language | English |
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Pages (from-to) | 4619-4624 |
Number of pages | 6 |
Journal | Journal of Organic Chemistry |
Volume | 66 |
Issue number | 13 |
DOIs | |
Publication status | Published - 29 Jun 2001 |
Externally published | Yes |
ASJC Scopus subject areas
- Organic Chemistry