Organolithium compounds are versatile intermediates in organic synthesis. However, their synthetic utility has been restricted due to their incompatibility with electrophilic functional groups such as esters. We have developed super silyl esters and utilized them for direct lithiation. Organolithium compounds bearing super silyl ester react with a variety of electrophiles and enable installation of useful functionality without a loss of the ester moiety. The reaction of lithiated super silyl chloroacetate with boron compounds achieves a-alkylation/arylation by Matteson rearrangement.

Generation of organolithium compounds bearing super silyl ester and its application to Matteson rearrangement

246th National Meeting (2013)

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