ipr
  Department of Chemistry
University of Utah
315 So. 1400 E. Rm. 4253A
Salt Lake City, UT 84112
sigman@chem.utah.edu
Office: (801) 585-0774


Seminar Schedule
 
 
 

 



Publications

 
Publication 56
 
     
 
Publication 55
 
     

(54) Miller, J.J.; Rajaran, S.; Pfaffenroth, C.; Sigman, M.S. "Synthesis of amine functionalized oxazolines with applications in asymmetric catalysis," Tetrahedron, 2009, 65, 3110-3119.

 
Image for Publication 54
 
     

(53) Michel, B. W.; Camelio, A. M; Cornell, C. N.; Sigman, M. S.* "A General and Efficient Catalyst System for a Wacker-Type Oxidation Using TBHP as the Terminal Oxidant: Application to Classically Challenging Substrates," J. Am. Chem. Soc.2009, 131, 17, 6076-6077.

 
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(51) Jensen, K. H.; Sigman, M. S.* "Mechanistic Approaches to Palladium-Catalyzed Alkene Difunctionalization Reactions," Org. Biomol. Chem. 2008, 8, 4083-4088.

 
Publication 51 Image
 
     

(50) Iwai, Y.; Gligorich, K. M.; Sigman, M. S. "Aerobic Alcohol Oxidation Coupled to Palladium-Catalyzed Alkene Hydroarylation with Boronic Esters,” Angew. Chem., Int. Ed. 2008, 47, 3219-3222.

 
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(48) Gligorich, K. M.; Cummings, S. A.; Sigman, M. S. "Palladium-Catalyzed Reductive Coupling of Styrenes and Organostannanes under Aerobic Conditions,” J. Am. Chem. Soc. 2007, 129, 14193-14195.

 
pub48
 
     
 
pub47
 
     

(46) Jensen, K. H. ; Sigman, M. S. "Systematically Probing the Effect of Catalyst Acidity in a Hydrogen-Bond-Catalyzed Enantioselective Reaction,” Angew. Chem., Int. Ed. 2007, 46, 4748-4750.

 
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pub44
 
     
(43) Cornell, C. N.; Sigman, M. S. “Recent Progress in Wacker Oxidations:  Moving Toward Molecular Oxygen as the Sole Oxidant,” Inorg. Chem. 2007, 46, 1903-1909.
 
pub43
 
 
(42) Gligorich, K. M.; Sigman, M. S. "Mechanistic Questions about the Reaction of Molecular Oxygen with Palladium in Oxidase Catalysis," Angew. Chem., Int. Ed. 2006, 45, 6612-6615.
 
pub42
 
 
(41) Schultz, M. J.; Sigman, M. S. "Recent Advances in Homogeneous Transition Metal-Catalyzed Aerobic Alcohol Oxidations," Tetrahedron 2006, 62, 8227-8241.
 
pub41
 
(40) Dible, B. R.; Sigman, M. S. "Steric Effects in the Aerobic Oxidation of Π-Allylnickel(II) Complexes with N-Heterocyclic Carbenes," Inorg. Chem. 2006, 45, 8430-8441.
 
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(38) Cornell, C. N.; Sigman, M. S. “Discovery of a Practical Direct O2-Coupled Wacker Oxidation using Pd[(-)-Sparteine]Cl2,” Org. Lett. 2006, 8, 4117-4120.
 
pub38
 
(37) Sigman, M. S.; Jensen, D. R. "Ligand-Modulated Palladium-Catalyzed Aerobic Alcohol Oxidations," Acc. Chem. Res. 2006, 39, 221-229.
 
pub37
 
 
(36) Balija, A. M.; Stowers, K. J.; Schultz, M. J.; Sigman, M. S. "Pd(II)-Catalyzed Conversion of Styrene Derivatives to Acetals: Impact of (-)-Sparteine on Regioselectivity," Org. Lett. 2006, 8, 1121-1124.
 
pub36
 
(35) Gligorich, K. M.; Schultz, M. J.; Sigman, M. S. "Palladium(II)-Catalyzed Aerobic Hydroalkoxylation of Styrenes Containing a Phenol,"  J. Am. Chem. Soc. 2006, 128, 2794-2795.
 
pub35
 
 
(34) Schultz, M. J.; Sigman, M. S.  "Palladium(II)-Catalyzed Aerobic Dialkoxylation of Styrenes: A Profound Influence of an o-Phenol,"  J. Am. Chem. Soc. 2006, 128, 1460-1461.
 
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(32) Mueller, J. A.; Cowell, A.; Chandler, B. D.; Sigman, M. S. "Origin of Enantioselection in Chiral Alcohol Oxidation Catalyzed by Pd[(-)-sparteine]Cl2," J. Am. Chem. Soc. 2005, 127, 14817-14824.
 
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(30) Schultz, M. J.; Adler, R. S.; Zierkiewicz, W.; Privalov, T.; Sigman, M. S. "Using Mechanistic and Computational Studies to Explain Ligand Effects in the Palladium-Catalyzed Aerobic Oxidation of Alcohols," J. Am. Chem. Soc. 2005, 127, 8499-8507.
 
pub30
 
(29) Dible, B. R.; Sigman, M. S.; Arif, A. M. "Oxygen-Induced Ligand Dehydrogenation of a Planar Bis-µ-Chloronickel (I) Dimer Featuring an NHC Ligand," Inorg. Chem. 2005, 44, 3774-3776.
 
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(27) Mercer, G. J.; Sturdy, M.; Jensen, D. R.; Sigman, M. S. "Intermolecular Reductive Coupling of Hindered N-aryl Imines Towards the Modular Synthesis of Chiral N-Heterocyclic Carbenes," Tetrahedron 2005, 61, 6418-6424.
 
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(26) Schultz, M. J.; Hamilton, S. S.; Jensen, D. R.; Sigman, M. S. "Development and Comparison of Substrate Scope of Pd-Catalysts for the Aerobic Oxidation of Alcohols," J. Org. Chem. 2005,  70, 3343-3352.
 
pub26
 
 
(25) Sigman, M. S.; Schultz, M. J. "The Renaissance of Palladium(II)-Catalyzed Oxidation Chemistry," Org. Biomol. Chem. 2004, 2, 2551-2554 (invited contribution).
 
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(23) Jensen, D. R.; Schultz, M. J.; Mueller, J. A.; Sigman, M. S. "Well-Defined Complex for Palladium-Catalyzed Aerobic Oxidation of Alcohols: Design, Synthesis, and Mechanistic Considerations," Angew. Chem. Int. Ed. 2003, 42. 3810-3813.
 
pub23
 
 
(22) Mandal, S. K.; Sigman, M. S. "Palladium-Catalyzed Aerobic Oxidative Kinetic Resolution of Alcohols Using an Achiral Exogenous Base," J. Org. Chem, 2003, 68, 7535-7537.
 
pub22
 
(21) Mandal, S. K. Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. "Scope of Enantioselective Palladium(II)-Catalyzed Aerobic Alcohol Oxidations Using (-)-Sparteine," J. Org. Chem. 2003, 68, 4600-4603.
 
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(19) Mercer, G. J.; Sigman, M. S. "Diastereoselective Synthesis of Piperazines by Manganese-Mediated Reductive Cyclization," Org. Lett. 2003, 5 1591-1594.
 
pub19
 
 
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(17) Dible, B. R.; Sigman, M. S. "Unusual Reactivity of Molecular Oxygen with π-Allylnickel(N-Heterocyclic Carbene) Chloride Complexes," J. Am. Chem. Soc. 2003, 125, 872-873;  An Editors’ Choice in Science 2003, 299, 313.
 
pub17
 
 
(16) Schultz, M. J.; Park, C. C.; Sigman, M. S. "A Convenient Pd-Catalyzed Aerobic Oxidation of Alcohols at Room Temperature," Chem. Commun. 2002, 3034-3035.
 
pub16
 
(15) Sigman, M. S.; Jensen, D. J.; Rajaram, S. "Enantioselective Oxidations Using Molecular Oxygen," Curr. Opin. Drug Discovery & Development, 2002, 5, 860-869 (invited contribution).
 
pub15
 
(14) Rajaram, S.; Sigman, M. S. "Modular Synthesis of Amine-Functionalized Oxazolines," Org. Lett2002,4, 3399-3401.
 
pub14
 
 
(13) Mueller, J. A.; Jensen, D. R.; Sigman, M. S. "Dual Role of (-)-Sparteine in the Palladium-Catalyzed Aerobic Oxidative Kinetic Resolution of Secondary Alcohols," J. Am. Chem. Soc. 2002, 124, 8202-8203.
 
pub13
 
 
(12) Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. "Palladium-Catalyzed Enantioselective Oxidations of Alcohols Using Molecular Oxygen," J. Am. Chem. Soc. 2001, 123, 7475-7476; Science Concentrate in Chem & Eng. News 2001, 79 (21), 40; Highlighted in Chemtracts by Kenneth M Nicholas Chemtracts 2001, 14, 654-658.
 
pub12
 
(11) Sigman, M. S.; Vachal, P.; Jacobsen E. N. "A General Catalyst for the Asymmetric Strecker Reaction" Angew. Chem. Int. Ed. 2000, 39, 1279-1281.
 
(10) Sigman, M. S.; Jacobsen, E. N. "Enantioselective Addition of Hydrogen Cyanide to Imines Catalyzed by a (salen)-Al Complex," J. Am. Chem. Soc. 1998, 120, 5315-5316.
 
(9) Sigman, M. S.; Fatland, A. W.; Eaton, B. E. "Cobalt-Catalyzed Cyclotrimerization of Alkynes in Aqueous Solution," J. Am. Chem. Soc. 1998, 120, 5130-5131.
 
 
(7) Sigman, M. S.; Eaton, B. E. "Iron Carbonyl Mediated [4 + 1] Cycloaddition of Diallenes and Carbon Monoxide," J. Am. Chem. Soc. 1996, 118 , 11783-11788.
 
(6) Sigman, M. S.; Eaton, B. E.; Heise, J. D.; Kubiak, C. P. "Low Temperature Study of the Catalytic Iron Mediated [4 + 1] Cyclization of Allenyl Ketones with Carbon Monoxide," Organometallics, 1996, 15, 2829-2832.
 
 
 
(3) Sigman, M. S.; Eaton, B. E. "Addition of Primary Amines to Conjugated Allenyl Aldehydes and Ketones," Tetrahedron Lett. 1993, 34, 5367-5368.
 
(2) Sigman, M. S.; Kerr, C. E.; Eaton, B. E. "Catalytic Iron-Mediated Carbon-Oxygen and Carbon-Carbon Bond Formation in [4 + 1] Assembly of Alkylidenebutenolides," J. Am. Chem. Soc. 1993, 115, 7545-7546.
 
 
   
  © 2007 The Sigman Group