The reaction of 2,2-dibromo-1-methyl-cyclopropanecarbonitrile (1) with i-PrMgCl in Et(2)O/CH(2)Cl(2) provides the cis-magnesium-carbenoid (2), which reacts with high retention of configuration with various electrophiles. If E = SPh, a stereoselective generation of a quaternary center via a sequential Br/Mg- and sulfoxide/Mg-exchange can be achieved. [reaction: see text]
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Kopp et al. (2005) studied this question.
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