Stereospecific Construction of Chiral Tertiary and Quaternary Carbon by Nucleophilic Cyclopropanation with Bis(iodozincio)methane
作者:Kenichi Nomura、Seijiro Matsubara
DOI:10.1002/asia.200900289
日期:2010.1.4
The reaction of a ketone having a leaving group at the α‐position, such as α,β‐epoxy ketone or α‐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
A process for the manufacture of aldehydes of the general formula ##EQU1## in which the symbols R.sub.1, R.sub.2 and R.sub.3 stand for hydrogen or organic radicals and in which at least two of these radicals are linked together by fragmenting a corresponding aziridine compound of the general formula ##EQU2## in which R.sub.1, R.sub.2 and R.sub.3 are as above and R.sub.4 to R.sub.7 each represents hydrogen, an alkoxycarbonyl, cyano, nitro or sulphonyl group or an alkyl, alkenyl, cycloalkenyl or alkyl residue and two or more of these residues may be linked together with simultaneous evolution of nitrogen.