The hydroformylation of methyl methacrylate (1) or t-butyl methacrylate (2) takes place with fair to good chemoselectivity, the regioselectivity depending on the catalyst precursor used. By contrast, methacrylonitrile (3), methacrylamide (4), and N-benzyl-methacrylamide (5) undergo hydroformylation followed by subsequent reactions. The formyl product formed is reduced to the corresponding 2-cyano-2-methylpropan-1-ol in the case of 3, and undergoes cyclization to 2-methyl-2,3-dehydrobutyrolactames for 4 and 5. Under conditions of hydrocarbalkoxylation in the presence of palladium catalysts, 4 gives 3-methylsuccinimide. In the enantioselective reactions, extents of asymmetric induction of about 20-50% have been obtained.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
- Materials Chemistry