title: A general diastereoselective catalytic vinylogous aldol reaction among tetramic acid-derived pyrroles.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Santa Barbara, California 93106, United States.
authors.forename: Jonathan G
authors.initials: JG
authors.lastname: David
authors.forename: Wen-Ju
authors.initials: WJ
authors.lastname: Bai
authors.forename: Marisa G
authors.initials: MG
authors.lastname: Weaver
authors.forename: Thomas R R
authors.initials: TR
authors.lastname: Pettus
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D011758:Pyrroles; D011760:Pyrrolidinones; C009435:tetramic acid; C116609:3-hydroxybutanal