Recent progress in the asymmetric Mannich reaction

Abstract

KEYWORDSThe asymmetric Mannich reaction is one of the most useful carbon-carbon bond forming reactions for the synthesis of chiral molecules containing nitrogen. The resulting β-amino carbonyl compounds are valuable synthons in the preparation of many natural products with useful biological properties. In recent years, asymmetric Mannich processes have increasingly been reported and used in a rapidly growing number of applications. This review provides an overview of the recent history of the applications of various catalytic systems in asymmetric Mannich reaction, including metal-based asymmetric organocatalysis, asymmetric organocatalysis, other chiral catalysis and no chiral catalysis systems. Chiral amine catalysis Chiral Bronsted acid Asymmetric organocatalysis Metal-based organocatalysis Asymmetric Mannich reaction Diastereo-and enantioselective

A Data-Driven Workflow for Assigning and Predicting Generality in Asymmetric Catalysis

“…In this first stage of developing an unsupervised learning platform, we sought to identify a “privileged” reaction type in catalysis wherein many different catalyst chemotypes had been employed. As imine electrophiles and carbonyl nucleophiles are amenable to a variety of catalytic modes of activation, we identified the organocatalytic Mannich reaction as the unifying reaction platform (Figure A). − This reaction type provides a wide range of both substrate and catalyst structures from published sources. We curated a data set consisting of 3003 reactions from 106 publications wherein diverse chiral H-bonding (1418 reactions), Brønsted acid (256 reactions), covalent catalysts (1182 reactions), and miscellaneous catalysts (147 reactions) had been employed (Figure ).…”

An Unsupervised Machine Learning Workflow for Assigning and Predicting Generality in Asymmetric Catalysis

“…As imine electrophiles and carbonyl nucleophiles are amenable to a variety of catalytic modes of activation, we identified the organocatalytic Mannich reaction as the unifying reaction platform (Figure 3A). [23][24][25][26] This reaction type provides a wide range of both substrate and catalyst structures from published sources. We curated a dataset consisting of 3003 reactions from 106 publications wherein diverse chiral H-bonding (1418 reactions), Brønsted acid (256 reactions), covalent catalysts (1182 reactions), and miscellaneous catalysts (147 reactions) had been employed (Figure 3).…”

An Unsupervised Machine Learning Workflow for Assigning and Predicting Generality in Asymmetric Catalysis

“…As imine electrophiles and carbonyl nucleophiles are amenable to a variety of catalytic modes of activation, we identified the organocatalytic Mannich reaction as the unifying reaction platform (Figure 3A). [22][23][24][25] This reaction type provides a wide range of both substrate and catalyst structures from published sources. We curated a dataset consisting of 3003 reactions from 106 publications wherein diverse chiral H-bonding (1418 reactions), Brønsted acid (256 reactions), covalent catalysts (1182 reactions), and miscellaneous catalysts (147 reactions) had been employed (Figure 3).…”