The Asymmetric Petasis Borono-Mannich Reaction: Insights on the Last 15 Years

Abstract

The Petasis borono-Mannich reaction, commonly described as the Petasis reaction, was one of the latest famous multicomponent reactions described in the literature. Currently celebrating its 30th anniversary since it was first reported by Petasis and Akritopoulou in 1993, this reaction has emerged as a powerful tool for the synthesis of biologically relevant molecules (such as substituted amines or amino acids), among others. This three-component catalyst-free reaction (the classic model), involving the coupling of an aldehyde, an amine, and a boronic acid, enables the synthesis of polysubstituted amine-containing molecules. Several accounts regarding the catalyst-free version using different carbonyl, amine, and boron-type components have been reported thus far. In contrast, the asymmetric version is still in its infancy since it was first reported in 2007. In this work, we aim to review the asymmetric versions of the Petasis reaction reported over the last 15 years, considering the chiral pool approach (asymmetric induction by one reaction component) and the use of catalysts (organocatalysts, transition-metal catalysts, and others) to access enantiomeric and diastereomeric pure amino-derivatives. Insights regarding the catalyzed Petasis reaction and consequent sustainable synthesis will be highlighted.