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2.16 Mannich Reaction

DOI: 10.1055/sos-SD-202-00407

Burns, N. Z.; Jacobsen, E. N.Science of Synthesis: Stereoselective Synthesis, (20112785.

General Introduction

The Mannich reaction is a classic organic transformation involving addition of a carbonyl enolate or equivalent to an imine, which may be preformed or generated in situ by condensation of an amine with an aldehyde or ketone. The product β-amino carbonyl compound, known as a Mannich base, is an indispensable building block for the construction of synthetically useful nitrogen-containing small molecules. Such compounds have been utilized in the synthesis of medicinal agents, natural products, and biological probes. Furthermore, the stereoselective Mannich reaction makes it possible to control the absolute and relative stereochemistry of the two contiguous carbon centers being joined by the newly formed bond.[‌1‌] This review will focus on recent and useful methods that have been developed to accomplish enantio- and diastereoselective Mannich reactions, including the variant known as the nitro-Mannich (also referred to as the aza-Henry) reaction. The related aza-BaylisHillman reaction is covered in Section 2.15.

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