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2.13.2.3 Nitroaldol Reactions

DOI: 10.1055/sos-SD-202-00331

Yliniemelä-Sipari, S. M.; Pihko, P. M.Science of Synthesis: Stereoselective Synthesis, (20112661.

Aliphatic nitro compounds enolize more readily than aliphatic ketones or aldehydes. In water, the pKa of nitromethane is ca. 10, whereas the pKa of acetone is 19.1.[‌31‌] In addition, the nitro group cannot act as an electrophile in aldol-type reactions; the enolized nitro compounds always act as nucleophiles and readily add to aldehydes in a process called the nitroaldol reaction. The nitroaldol, or Henry reaction, named after L. Henry who discovered the reaction in 1895,[‌171‌] is a particularly attractive method for the stereoselective construction of CC bonds.[‌172‌‌175‌] The product is a β-nitro alcohol (nitroaldol). The nitro alcohol products can be transformed into a number of valuable nitrogen- and oxygen-containing derivatives such as nitroalkanes, amino alcohols, and carboxylic acids.

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