Morita–Baylis–Hillman (MBH) Reaction Derived Nitroallylic Alcohols, Acetates and Amines as Synthons in Organocatalysis and Heterocycle Synthesis

• Published in: Chemical record Vol. 17; no. 3; pp. 363 - 381
• Main Authors: Huang, Wan‐Yun, Anwar, Shaik, Chen, Kwunmin
• Format: Journal Article
• Language: English
• Published: United States Wiley Subscription Services, Inc 01.03.2017
• Subjects: Alcohol; asymmetric synthesis; heterocycles; nitroallylic alcohols; organocatalysis; sequential reaction; organocatalysis; nitroallylic alcohols; sequential reaction; asymmetric synthesis; heterocycles
• ISSN: 1527-8999; 1528-0691
• DOI: 10.1002/tcr.201600075

The Morita–Baylis–Hillman (MBH) reaction is one of the most useful and efficient protocols for constructing new carbon–carbon bonds between an activated olefin and electrophiles in the presence of a tertiary amine/phosphine. Herein, we present the use of MBH alcohols, which are obtained from the reaction of nitrostyrenes with aldehydes, as well as acetates and amines derived thereof in several organocatalytic transformations. Densely functionalised MBH adducts can also be used to synthesise substituted heteroaromatic compounds, such as furan, pyrrole, pyrazole and imidazole derivatives. Making bonds: The Morita–Baylis–Hillman reaction of nitroallylic alcohols and derived acetates and amines have been utilised in asymmetric catalysis and heterocycle synthesis. These adducts are useful synthons in organocatalysis that involves cascade reactions, kinetic resolution, and desymmetrisation. In addition, these substrates can also be used for the construction of numerous substituted heterocycles.