The Boronic Acid Mannich Reaction

Abstract

The boronic acid Mannich reaction is a three-component reaction between a carbonyl compound (aldehyde or ketone), an amine (primary or secondary) and a boronic acid. This chapter addresses the mechanism, stereochemistry, and the scope and limitations of each of the three components of this reaction. Some typical experimental conditions are provided along with a comprehensive Tabular Survey. This three-component reaction is extremely versatile for preparing important chiral starting materials for the synthesis of molecules of biological interest, including chiral α-amino acids, 1,2-amino alcohols, 2-aminoalkyl phenols, heterocycles, and alkaloids as shown in the general scheme below. Keywords: multicomponent reactions; Petasis reaction