Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 5, Issue 1, Pages 147-152Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.200900289
Keywords
cycloaddition; ketones; nucleophilic addition; nucleophilic substitution; zinc
Categories
Funding
- Japanese Ministry of Education, Culture, Sports. Science, and Technology
- Kyoto University
- International Innovation Center
- Global COE Program Integrated Materials Science [B-09]
- Japan Society for the Promotion of Science
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The reaction of a ketone having a leaving group at the alpha-position, such as alpha,beta-epoxy ketone or alpha-sulfonyloxy ketone, with bis(iodozincio)methane affords a zinc alkoxide of cyclopropanol. The reaction proceeds by nucleophilic addition of the dizinc to the carbonyl group and a sequential intramolecular nucleophilic substitution of the introduced iodozinciomethyl group to the adjacent electrophilic carbon that has a leaving group. When an optically active alpha,beta-epoxy ketone or alpha-sulfonyloxy ketone is treated with the dizinc, a zinc alkoxide of cyclopropanol having a chiral tertiary or quaternary carbon in the cyclopropane ring is obtained, and the obtained zinc alkoxide of cyclopropanol acts as a chiral homoenolate. When it is treated with an electrophile in the presence of copper cyanide, it gives an optically active alpha-tertiary or -quaternary ketone that retains high optical purity.
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