title: Diazoacetoacetate enones for the synthesis of diverse natural product-like scaffolds.
abstract: Diazoacetoacetate enones are a new class of Michael acceptors that enable the efficient construction of natural product-like scaffolds. Through their Michael addition reactions, including those with silyl enol ethers, indoles, pyrroles, and amines, δ-functionalized diazoacetoacetates are formed in high yield and with overall operational efficiency. Subsequent catalytic dinitrogen extrusion reactions provide access to a diverse series of natural product-like carbo- and heterocyclic ring systems in only three steps from commercial materials.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
authors.forename: Charles S
authors.initials: CS
authors.lastname: Shanahan
authors.forename: Phong
authors.initials: P
authors.lastname: Truong
authors.forename: Savannah M
authors.initials: SM
authors.lastname: Mason
authors.forename: John S
authors.initials: JS
authors.lastname: Leszczynski
authors.forename: Michael P
authors.initials: MP
authors.lastname: Doyle
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*; D014226:Triazenes / Q000737:chemistry*
chemical_list: D000438:Alcohols; D001688:Biological Products; D006571:Heterocyclic Compounds; D007211:Indoles; D011758:Pyrroles; D014226:Triazenes