120284-29-9Relevant academic research and scientific papers
Preparation of zinc-homoenolate from α-sulfonyloxy ketone and bis(iodozincio)methane
Nomura, Kenichi,Matsubara, Seijiro
, p. 164 - 165 (2007)
Treatment of α-sulfonyloxy ketone with bis(iodozincio)-methane gives a zinc cyclopropoxide which is formed via a nucleophilic addition of the reagent to carbonyl group followed by an intramolecular substitution reaction. Copyright
Stereospecific construction of chiral tertiary and quaternary carbon by nucleophilic cyclopropanation with bis(iodozincio)methane
Nomura, Kenichi,Matsubara, Seijiro
supporting information; experimental part, p. 147 - 152 (2010/04/23)
The reaction of a ketone having a leaving group at the aposition, such as a,bepoxy ketone or asulfonyloxy 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 a,β-epoxy ketone or asulfonyloxy 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 ho-moenolate. When it is treated with an electrophile in the presence of copper cyanide, it gives an optically active a-tertiary or -quaternary ketone that retains high optical purity.
