Iron-catalyzed synthesis of β-1,3-dicarbonyl aldehydes
I must confess that I’ve been drawn to any publication in which the authors use Fe2(CO)9. This is probably because my grad school advisor made do the photodimerization of Fe(CO)5 instead of buying it. Ah, the beauty of pyrophoric iron bursting into flames in the frit in front of my face! Such memories!
Li and coworkers have described (DOI: 10.1021/ol202749x) a process by which a variety of 3° amines serve as an enone synthon, undergoing Michael addition reactions to form the title compounds:
The iron catalyst is responsible for conversion of two equivalents of the amine to the enone, utilizing a version of the Polonovski reaction as described by Scammells and coworkers:
Altogether, the authors report 18 examples of the reaction with isolated yields ranging from 12% to 69%.
i heart d-orbitals 