New Synthetic Methods for the Construction of Organic Molecules Based on the Chemistry of Magnesium Carbenoids

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Carbenes and carbenoids have been known to be highly reactive carbon species that show a variety of unique reactivities. However, those reactive species are not fully used in organic synthesis. In order to solve the problem mentioned above, we used aryl α-haloalkyl (or alkenyl) sulfoxides as the precursors and used sulfoxide-magnesium exchange reaction for generation of much mild magnesium carbenoids (alkylmagnesium carbenoids, magnesium alkylidenecarbenoids, cyclopropylmagnesium carbenoids and cyclobutylmagnesium carbenoids). From the investigation of their nature and reactivity, a variety of novel new synthetic reactions were found and established. In addition, it was established that the method for a synthesis of aryl α-chloroalkyl sulfoxides in optically active form. New asymmetric synthesis of organic molecules was successfullyobtained by using these optically active α-chloroalkyl sulfoxides.