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Keywords:

  • arylation;
  • matteson rearrangement;
  • organolithium reagents;
  • super silyl;
  • synthetic methods
Thumbnail image of graphical abstract

It's super-silyl-fragilithyl-ester-aryl-docious: The super silyl group is a strong protecting group for carboxylic acids and provides a method for direct lithiation that is compatible with the ester moiety. Organolithium compounds bearing a super silyl ester react with a variety of electrophiles in high yields (see scheme). The reaction of lithiated super silyl chloroacetate with a boron compound gives α-functionalization of the ester moiety by Matteson rearrangement.