Boron-Catalyzed Nucleophilic Activation of Carboxylic Acids

The carboxyl group is a ubiquitous chemical function present in a very large number of compounds essential for life itself (such as amino acids and fatty acid derivatives) as well as in countless bioactive molecules, natural compounds and drugs. The development of efficient methods for achieving the structural modification and homologation of carboxylic acid derivatives without requiring the use of protecting groups continues to attract a great deal of interest in organic chemistry. In particular, novel carbon–carbon bond-forming reactions allowing for a stereocontrolled and direct functionalization of carboxylic acids are in great demand. Recently, the group of Professor Motomu Kanai at The University of Tokyo’s Graduate School of Pharmaceutical Sciences (Japan) has developed a method for generating carboxylic acid derived enolates under mild conditions, and extended this method to the first carboxylic acid selective catalytic Mannich-type reaction.

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