UC Santa Barbara
A General Diastereoselective Catalytic Vinylogous Aldol Reaction Among Tetramic Acid-Derived Pyrroles
- Author(s): David, Jonathan Gene
- Advisor(s): Pettus, Thomas R R
- et al.
A catalytic diastereoselective aldol reaction has been developed for N1-arylated/C2-O-silylated/C3-methylated and brominated/C4-O-methylated pyrroles in its reactions with various aldehydes. Syn adducts emerge with regard to the vicinal nitrogen and oxygen heteroatom substituents. The N1-aryl residue undergoes oxidative cleavage, and the C3- bromine atom undergoes palladium-mediated coupling reactions, both without disturbing the newly created stereocenters.