Generation of unstable carbanions by ligand exchange reaction of sultoxides and application to new synthetic method

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Development of new synthetic methods by the ligand exchange reaction of sulfoxides were investigated and several new interesting results were obtained ; those are as follows.1.The reaction of sulfinyl aziridines with t-BuLi resulted in formation of aziridinyllithium in good yields. The property and synthetic application to alpha-dialkylamino acid derivatives were studied.2.Oxiranyllithium having carbanion destabilizing group (alkyl groups) were abled to be generated by the ligand exchange reaction of sulfinyloxirans. Property and applications to new synthetic method of epoxides and alcohols including optically active form were developed.3.alpha-Halovinyl sulfoxides were found to react with Grignard reagents to give magnesium alkylidene carbenoids. A new synthetic method for tetra-substituted olefins was realized by this reaction.4.A new method for one-carbon homologation of methylesters was realized and the method was applied to one-carbon ring expansion of lactones and to a homologation of alpha, beta-unsaturated aldehydes.5.Sulfoxide version of Julia-Lythgou olefination was realized via the ligand exchange reaction of beta-mesyloxy sulfoxides.