研究领域

Catalytioxidatioprocesse ;Desigandevelopmenochiracatalyst ;Diazchemistr ;Highlenantioselectivcatalytireaction ;Medicinachemistry

The major focus of our research program is the development of highly selective and efficient catalytic processes for the synthesis of biologically relevant compounds. Investigations are built upon unique, highly efficient and selective, catalytic uses of dirhodium and other transition metal catalysts. We are developing diazo chemistry for catalytic highly stereoselective transformations to further enhance the applicability of catalytic metal carbene chemistry in organic synthesis. Lewis acidic chiral dirhodium(II,III) carboxamidate catalysts are being used to broaden the range of asymmetric Lewis acid catalyzed carbon-carbon bond forming transformations. Catalytic oxidative methodologies to prepare compounds that are of biological significance are being developed; applications encompass reactions with steroids, phenolic compounds, unsaturated fatty acid derivatives, terpenes, amines, and other biologically relevant substrates.

近期论文

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Liu, Y.; Deng, Y.; Liu, R.; Doyle, M.P. ""An Efficient Route to Highly Enantioenriched Tetrahydroazulenes and β-Tetralones by Desymmetrization Reactions of δ,δ-Diaryldiazoacetoacetates"" Chem. Commun. 2015, 51, 565-568. Angelone, D.; Draksharapu, A.; Browne, W.R.; Choudhuri, M.M.R.; Crutchley, R.J.; Xu, X.; Xu, X; Doyle, M.P. ""Dinuclear Compounds Without a Metal-Metal Bond. Dirhodium(III,III) Carboxamidates"" Inorg. Chim. Acta 2015, 424, 235-240. Xu, X.; Wang, X.; Liu, Y.; Doyle, M.P. ""Enantioselective Carbonyl-ene Reactions Catalyzed by Chiral Cationic Dirhodium(II,III) Carboxamidates"" J. Org. Chem. 2014, 79, 12185-12190. Wilson, Z.S.; McGuire, S.Y.; Limbach, P.A.; Doyle, M.P.; Marzilli, L.G.; Warner, I.M. “Diversifying Science, Technology, Engineering, and Mathematics (STEM) – An empirical inquiry into successful approaches in chemistry” J. Chem. Educ. 2014, 91, 1860-1866. Ratnikov, M.O.; Doyle, M.P. ""Dirhodium caprolactamate and tert-butyl hydroperoxide -- a universal system for selective oxidations"" Mendeleev Commun. 2014, 24, 187-252. Liu, X.; Liu, X.; Shanahan, C.S.; Xu, X.; Doyle, M.P. ""A Survey of Enoldiazo Nucleophilicity in Selective C-C Bond Forming Reactions for the Synthesis of Natural Product-Like Frameworks"" Org. & Biomol. Chem. 2014, 12, 5227-5234. Truong, P.M.; Zavalij, P.Y.; Doyle, M.P. ""Highly Enantioselective Carbonyl-Ene Reactions of 2,3-Diketoesters; Efficient and Atom-Economical Process to Functionalized Chiral α-Hydroxy-β-ketoesters"" Angew. Chem. Int. Ed. 2014, 53, 6468–6472. Xu, X.; Doyle, M.P. ""The [3+3]-Cycloaddition Alternative for Heterocycle Syntheses: Catalytically Generated Metalloenolcarbenes as Dipolar Adducts"" Acc. Chem. Res. 2014, 47, 1396-1405. Xu, X.; Leszczynski, J.S.; Mason, S.M.; Zavalij, P.Y.; Doyle, M.P. ""Expedient Access to Substituted 3-Amino-2-cyclopentenones by Dirhodium-catalyzed [3+2]-Annulation of Silylated Ketene Imines and Enoldiazoacetates"" Chem. Commun. 2014, 50, 2462-2464. Mandler, M.D.; Truong, P.M.; Zavalij, P.Y.; Doyle, M.P. ""Catalytic Conversion of Diazocarbonyl Compounds to Imines: Applications to the Synthesis of Tetrahydropyrimidines and β-Lactams"" Org. Lett. 2014, 16, 740-743. Truong, P.M.; Mandler, M.D.; Shanahan, C.S.; Doyle, M.P. ""Lewis Acid Catalyzed Diastereoselective 1,3-Dipolar Cycloaddition Between Diazoacetacetate Enones and Azomethine Ylides"" Heterocycles 2014, 88, 1039-1049. Xu, X.; Doyle, M.P. ""Recent Developments in the Synthetic Uses of Silyl-protected Enoldiazoacetates for Heterocyclic Syntheses"" Austral. J. Chem. 2014, 67, 365-373. Xu, X.; Zavalij, P.Y.; Doyle, M.P. ""Highly Enantioselective Dearomatizing Formal [3+3]-Cycloaddition Reactions of N-Acyliminopyridinium Ylides with Electrophilic Enolcarbene Intermediates"" Angew. Chem. Int. Ed. 2013, 52, 12664-12668. Xu, X.; Zavalij, P.Y.; Doyle, M.P. ""Catalytic Asymmetric Syntheses of Quinolizidines by Dirhodium-catalyzed Dearomatization of Isoquinolinium/Pyridinium Methylides – The Role of Catalyst and Carbene Source"" J. Am. Chem. Soc. 2013, 135, 12439-12447. Ratnikov, M.O.; Xu, X.; Doyle, M.P. ""Simple and Sustainable Iron-Catalyzed Aerobic C-H Functionalization of N,N-Dialkylanilines"" J. Am. Chem. Soc. 2013, 135, 9475-9479. Xu, X.; Qian, Y.; Zavalij, P.Y.; Doyle, M.P. ""Highly Selective Catalyst-Dependent Competitive 1,2-C→C, -O→C and -N→C Migrations from β-Methylene-β-silyloxy-β-amido-α-Diazoacetates"" J. Am. Chem. Soc. 2013, 135, 1244-1247. Ratnikov, M.O.; Doyle, M.P. ""Mechanistic Investigation of Oxidative Mannich Reaction with tert-Butyl Hydroperoxide. The Role of Transition Metal Salt"" J. Am. Chem. Soc. 2013, 135, 1549-1557.