Professor Krische's research focuses on the development of new synthetic methods with attendant applications in natural product synthesis. A central theme of his program involves the identification of new reactivity patterns, the evolution of related catalytic processes and, ultimately, the development of new synthetic strategies. His research program encompasses organic synthesis, catalysis, organometallic chemistry, and supramolecular chemistry. In this context, a broad family of catalytic C-C bond formations have been developed, these include the following:

Hydrogen Mediated C-C Bond Formation

"Iridium Catalyzed anti-Diastereo- and Enantioselective Carbonyl (Trimethylsilyl)allylation from the Alcohol or Aldehyde Oxidation Level" Han, S. B.; Gao, X.; Krische, M. J. J. Am. Chem. Soc. 2010,132, 9153.

"Direct Ruthenium Catalyzed C-C Coupling of Ethanol: Diene Hydro-Hydroxyethylation to Form All Carbon Quaternary Center" Han, H.; Krische, M. J. Org. Lett. 2010,12, 2844.

"Allenamide Hydro-Hydroxyalkylation: 1,2-Aminoalcohols via Ruthenium Catalyzed Carbonyl anti-Aminoallylation" Zbieg, J. R.; McInturff, E.; Krische, M. J. Org. Lett. 2010,12, 2514.

"anti-Diastereo- and Enantioselective Carbonyl (Hydroxymethyl)allylation form the Alcohol or Aldehyde Oxidation Level: Allyl Carbonates as Allylmetal Surrogates" Zhang, Y. J.; Yang, J. H.; Kim, S. H.; Krische, M. J. J. Am. Chem. Soc. 2010, 132, 4562.

"Diastereo- and Enantioselective anti-Alkoxyallylation Employing Allylic gem-Dicarboxylate as Ally Donors via Iridium Catalyzed Transfer Hydorgenation." Han, S. B.; Han, H.; Krische, M. J. J. Am. Chem. Soc. 2010, 132, 1760.

"All Carbon Quaternary Centers via Ruthenium Catalyzed Hydroxymethylation of 2-Substituted Butadiene Mediated by Formaldehyde: Beyond Hydroformylation." Smejkal, T.; Han, H.; Breit, B.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 10366.

"Enantioselective Allylation Crotylation and Reverse Prenylation of Substituted Isatin via Iridium Catalyzed C-C Bond Forming Transfer Hydrogenation." Itoh, J.; Han, S. B.; Krische, M. J. Angew. Chem. Int. Ed. 2009, 48, 6313.

"Elongation of 1,3-Polyols via Iterative Catalyst-Directed Carbonyl Allylation from the Alcohol Oxidation Level." Hassan, A.; Lu, Y.; Krische, M. J. Org. Lett. 2009, 11, 3112.

"1,n-Glycols as Dialdehyde Equivalents in Iridium Catalyzed Enantioselective Carbonyl Allylation and Iterative Two-Directional Assembly of 1,3-Polyols." Lu, Y.; Kim, I.-S.; Hassan, A.; Del Valle, D. J.; Krische, M. J. Angew. Chem. Int. Ed. 2009, 48, 5018.

"Enantioselective Carbonyl Reverse Prenylation from the Alcohol or Aldehyde Oxidation Level Employing 1,1-Dimethylallene as the Prenyl Donor." Han, S. B.; Kim, I.-S.; Han, H.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 6916.

"anti-Aminoallylation of Aldehydes via Ruthenium Catalyzed Transfer Hydrogenative Coupling of Sulfonamido Allenes: 1,2-Aminoalcohols ." Skucas, E.; Zbieg, J. R.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 5054.

“Direct C-Vinylation of Alcohols or Aldehydes Employing Alkynes as Vinyl Donors: A Ruthenium Catalyzed C-C Bond Forming Transfer Hydrogenation.” Patman, R. L.; Chaulagain, M. R.; Williams, V. M.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2066.

"anti-Diastereo- and Enantioselective Carbonyl Crotylation from the Alcohol or Aldehyde Oxidation Level Employing a Cyclometallated Iridium Catalyst: a-Methyl Allyl Acetate as a Surrogate to Preformed Crotylmetal Reagent." Kim, I. S.; Han, S. B.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2514.

"Hydroacylation of 2-Butyne from the Alcohol or Aldehyde Oxidation Level via Ruthenium Catalyzed C-C Bond Forming Transfer Hydrogenation." Williams, V. M.; Leung, J. C.; Patman, R. L.; Krische, M. J. Tetrahedron 2009, 65, 5024.

"Enantioselective Iridium Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level via Transfer Hydrogenative Coupling of Allyl Acetate: Departure from Chirally Modified Allyl Metal Reagents in Carbonly Addition." Kim, I. S.; Ngai, M. -Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14891.

"Diene Hydroacylation from the Alcohol or Aldehyde Oxidation Level via Ruthenium-Catalyzed C-C Bond-Forming Transger Hydrogenation: Synthesis of   -Unsaturated Ketones." Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14120.

"Branch-Selective Reductive Coupling of 2-Vinyl Pyridines and Imines via Rhodium Catalyzed C-C Bond Forming Hydrogenation." Komanduri. V.;Grant, C. D.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 12592.

"Catalyst-Directed Diastereoselectivity in Hydrogenative Coupling of Acetylene to a-Chiral Aldehydes: Formal Synthesis of All Eight L-Hexoses." Han, S. B.; Kong, J.-R.; Krische, M. J. Org. Lett. 2008, 10, 4133.

"Ruthenium Catalyzed C-C Bond Formation via Transfer Hydrogenation: Branch-Selective Reductive Coupling of Allenes to Paraformaldehyde and Higher Aldehydes." Ngai, M. -Y.; Skucas, E.; Krische, M. J. Org. Lett. 2008, 10, 2705.

"Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Enynes as Surrogates to Preformed Allenylmetal Reagents: A Ruthenium Catalyzed C-C Bond Forming Transfer Hydrogenation." Patman, R. L.; Williams, V. M.; Bower, J. F.; Krische, M. J. Angew. Chem. Int. Ed. 2008, 47, 5220.

"Enantioselective Iridium Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Using Allyl Acetate as an Allyl Metal Surrogate." Kim, I. S.; Ngai, M, -Y.;  Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6340.

"Ruthenium Catalyzed C-C Bond Forming Transfer Hydrogenation: Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Employing Acyclic 1,3-Dienes as Surrogates to Preformed Allyl Metal Reagents." Shibahara, F.; Bower, J. F.;  Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6338.

"Diastereo- and Enantioselective Hydrogenative Aldol Coupling of Vinyl Ketones: Design of an Effective Monodentate TADDOL-Like Phosphonite Ligand." Bee C.; Han, S. B.; Hassan, A.; Ioda, H.;  Krische, M.J. J. Am. Chem. Soc. 2008, 130, 2746.

"Iridium Catalyzed C-C Couplig via Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Cyclohexadiene." Bower, J. F.; Patman, R. L.; Krische, M.J. Org. Lett. 2008, 10, 1033.

"Catalytic C-C Coupling via Transfer Hydrogenation: Reverse Prenylation, Crotylation and Allylation from the Alcohol or Aldehyde Oxidation Level." Bower, J.; Skucas, E.; Patman, R. L.; Krische, M.J. J. Am. Chem. Soc. 2007, 129, 15134.

"Enantioselecetive Iridium Catalyzed Imine Vinylation: Optically Enriched Allylic Amines via Alkyne-Imine Reductive Coupling Mediated by Hydrogen." Ngai, M.-Y.; Barchuk, A.; Krische, M.J. J. Am. Chem. Soc. 2007, 129, 12644.

"Carbonyl Allylation in the Absence of Preformed Allyl Metal Reagents: Reverse Prenylation via Iridium Catalyzed Hydrogenative Coupling of Dimethylallene." Skucas, E.; Bower, J.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 12678.

"Enantioselective Reductive Coupling of 1,3-Enynes to Glyoxalates Mediated by Hydrogen: Asymmetric Synthesis of b,g-Unsaturated a-Hydroxy Esters."  Hong, Y.-T.; Cho, C.-W.; Skucas, E.; Krische, M. J. Org. Lett. 2007, 9, 3745.

"Allylic Amine via Iridium Catalyzed C-C Bond Forming Hydrogenation: Imine Vinylation in the Absence of Stoichiometric Byproducts or Metallic Reagents." Barchuk, A.; Ngai, M.-Y.; Krische, M.J. J. Am. Chem. Soc. 2007, 129, 8432.

"Enantioselective Reductive Coupling of Acetylene to N-Arylsulfonyl Imines via Rhodium Catalyzed C-C Bond Forming Hydrogenation: (Z)-Dienyl Allylic Amines." Skucas, E.; Kong, J.-R.; Krische, M.J. J. Am. Chem. Soc. 2007, 129, 7242.

"Iridium Catalyzed C-C Bond Forming Hydrogenation: Direct Regioselective Reductive Coupling of Alkyl-Substituted Alkynes to Activated Ketones." Ngai, M.-Y.; Barchuk, A.; Krische, M.J. J. Am. Chem. Soc. 2007, 129, 280.

"Asymmetric Induction in Hydrogen-Mediated Reductive Aldol Additions to   - Amino Aldehydes Catalyzed by Rhodium: Selective Formation of syn-Stereotriads Directed by Intramolecular Hydrogen-Bonding." Jung, C.-K.; Krische, M.J. J. Am. Chem. Soc. 2006, 128, 17051.

"Enantioselective Reductive Coupling of 1,3-Enynes to Heterocyclic Aromatic Aldehydes and Ketones via Rhodium Catalyzed Asymmetric Hydrogenation: Mechanistic Insight into the Role of BrØnsted Acid Additives." Komanduri, V.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16448.

"Catalytic Carbonyl (Z)-Dienylation via Multicomponent Reductive Coupling of Acetylene to Aldehydes and -Ketoesters Mediated by Hydrogen: Carbonyl Insertion into Cationic Rhodocyclopentadienes." Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16040.

"Branched-Selective Intermolecular Hydroacylation: Hydrogen-Mediated Coupling of Anhydrides to Styrenes and Activated Olefins." Hong, Y.-T.; Barchuk, A.; Krische, M. J. Angew. Chem. Int. Ed. 2006, 128, 6885.

"Reductive Aldol Coupling of Divinyl Ketones via Rhodium Catalyzed Hydrogenation: syn-Diastereoselective Construction of  -Hydroxyenones." Han, S. B.; Krische, M. J. Org. Lett. 2006, 8, 5657.

"Highly Enantioselective Reductive Cyclization of Acetylenic Aldehydes via Rhodium Catalyzed Asymmetric Hydrogenation." Rhee, J.-U.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 10674.

"a-Hydroxy Esters via Enantioselective Hydrogen-Mediated C-C Coupling: Regiocontrolled Reactions of Silyl-Substituted 1,3-Diynes." Cho, C.-W.; Krische, M. J. Org. Lett. 2006, 8, 3873.

"An Approach to the Bryostatin Recognition Domain via Enantioselective Rhodium Catalyzed Reductive Coupling Mediated by Hydrogen." Cho, C.-W.; Krische, M. J. Org. Lett. 2006, 8, 891.

"Hydrogen-Mediated Aldol Reductive Coupling of Vinyl Ketones Catalyzed by Rhodium: High Syn-Selectivity through the Effect of Tri-2-furylphosphine," Jung, C.-K.; Garner, S. A.; Krische, M. J. Org. Lett. 2006, 8, 519.

"Highly Enantioselective Direct Reductive Coupling of Conjugated Alkynes and a-Ketoesters via Rhodium Catalyzed Asymmetric Hydrogenation," Kong, J.-R.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718.

"Hydrogen-Mediated Reductive Coupling of Conjugated Alkynes with Ethyl (N-sulfinyl)iminoacetates: Diastereoselective Synthesis of Unnatural a-Amino Acids via Rhodium Catalyzed C-C Bond Forming Hydrogenation" Kong, J.-R.; Cho, C.-W.; Krische, M. J. J. Am. Chem. Soc. 2005, 127, 11269.

"Enantioselective Reductive Cyclization of 1,6-Enynes via Rhodium Catalyzed Asymmetric Hydrogenation: C-C Bond Formation Precedes Hydrogen Activation" Jang, H.-Y.; Hughes, F. W.; Gong, H.; Zhang, J.; Brodbelt, J. S.; Krische, M. J. J. Am. Chem. Soc. 2005, 127, 6174.

"Rhodium Catalyzed Reductive Cyclization of 1,6-Diynes and 1,6-Enynes Mediated by Hydrogen: Catalytic C-C Bond Formation via Capture of Hydrogenation Intermediates" Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 7875.

"Hydrogen-Mediated C-C Bond Formation: Catalytic Regio- and Stereoselective Reductive Condensation of a-Ketoaldehydes and 1,3-Enynes" Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4664.

"Catalytic Addition of Metallo-Aldehyde Enolates to Ketones: A New C-C Bond Forming Hydrogenation" Koech, P. K.; Krische, M. J. Org. Lett. 2004, 6, 691.

"Metallo-Aldehyde Enolates via Enal Hydrogenation: Catalytic Cross Aldolization with Glyoxal Partners as Applied to the Synthesis of 3,5-Disubstituted Pyridazines" Marriner, G. A.; Garner, S. A.; Jang, H.-Y.; Krische, M. J. J. Org. Chem. 2004, 69, 1380.

"First Catalytic Reductive Coupling of 1,3-Diynes to Carbonyl Partners: A New Regio- and Enantioselective C-C Bond Forming Hydrogenation" Huddleston, R. R.; Jang, H.-Y. Krische, M. J. J. Am. Chem. Soc. 2003, 125, 11488.

"Enolate Generation under Hydrogenation Conditions: Catalytic Aldol Cycloreduction of Keto-Enones" Huddleston, R. R.; Krische, M. J. Org. Lett. 2003, 5, 1143.

"Use of Elemental Hydrogen for the Reductive Generation of Enolates from Enones: Catalytic C-C Bond Formation under Hydrogenative Conditions" Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.

"Asymmetric Total Synthesis of the Iridoid -Glucoside (+)-Geniposide via Phosphine Organocatalysis." Jones, R. A.; Krische, M. J. Org. Lett. 2009, 11, In Press.

"Concise Stereocontrolled Formal Synthesis of (±)-Quinine and Total Synthesis of (±)-7-Hydroxyquinine via Merged Morita-Baylis-Hillman-Tsuji-Trost Cyclization." Webber, P.; Krische, M. J. J. Org. Chem. 2008, 73, 9379.

"Phosphine Catalyzed Allylic Substitution of Morita-Baylis-Hillman Acetates: Synthesis of N-Protected  -Aminophosphonic Acid Esters." Park, H.; Cho, C.-W.; Krische, M. J. J. Org. Chem. 2006, 71, 7892.

"Enatioselective Total and Formal Syntheses of Paroxetine (PAXIL) via Phosphine Catalyzed Enone -Arylation Using Arylbismuth (V) Reagents: A Regiochemical Complement to Heck Arylation." Koech, P. K.; Krische, M. J. Tetrahedron 2006, 62, 10594.

"Regio- and Stereoselective Construction of g-Butenolides via Phosphine Catalyzed Substitution of Morita-Baylis-Hillman Acetates: An Organocatalytic Allylic Alkylation" Cho, C.-W.; Krische, M. J. Angew. Chem. Int. Ed. 2004, 43, 6689.

"Phosphine Catalyzed Regiospecific Allylic Amination and Dynamic Kinetic Resolution of Morita-Baylis-Hillman Acetates" Cho, C.-W.; Kong, J. R.; Krische, M. J. Org. Lett. 2004, 6, 1337.

"Nucleophilic Catalysis via Phosphine Conjugate Addition: Vinyl Sulfones as Reacting Partners in Catalytic Cross-Michael Cycloisomerization" Luis, A.-L.; Krische, M. J. Synthesis (Feature Article), 2004, 2579.

"Phosphine Catalyzed a-Arylation of Enones Using Hypervalent Bismuth Reagents: Regiospecific Enolate Arylation via Nucleophilic Catalysis" Koech, P. K.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 5350.

"Phosphine Mediated Reductive Condensation of g-Acyloxy Butynoates: A Diversity Oriented Strategy for the Construction of Substituted Furans" Wang, J.-C.; Jung, C.-K.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118.

"Intramolecular Organocatalytic [3+2] Dipolar Cycloaddition: Stereospecific Cycloaddition and The Total Synthesis of (±)-Hirsutene" Wang, J.-C.; Krische, M. J. Angew. Chem. Int. Ed. 2003, 42, 5855.

"Catalytic Crossed Michael Cycloisomerization of Thioenoates: Total Synthesis of (±)-Ricciocarpin A" Agapiou, K.; Krische, M. J. Org. Lett. 2003, 5, 1737.

"Catalytic Enone Allylation via Concomitant Activation of Latent Nucleophilic and Electrophilic Partners: Merging Organic and Transition Metal Catalysis" Jellerichs, B. G.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 7758.

"Catalytic Diastereoselective Synthesis of Diquinanes from Acyclic Precursors" Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682.

"Organocatalytic Michael Cycloisomerization of bis(Enones): The Intramolecular Rauhut-Currier Reaction" Wang, L.-C.; Luiz, A.-L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.

"A Mechanistic Dichotomy in the Reaction of Gilman Reagents with Conjugated Enones: Partitioning of Electron Transfer and Conjugate Addition Manifolds" Yang, J.; Cauble, D. C.; Berro, A. J.; Bauld, N. L.; Krische, M. J. J. Org. Chem. 2004, 69, 7979.

"Chemically Induced Anion Radical Cycloadditions: Intramolecular Cyclobutanation of bis(Enones) via Homogeneous Electron Transfer" Yang, J.; Felton, G. A. N.; Bauld, N. L.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 1634.

"Diastereoselective Cycloreductions and Cycloadditions Catalyzed by Co(dpm)2/Silane (dpm = 2,2,6,6-tetramethyl-heptane-3,5-dionate): Mechanism and Partitioning of Hydrometallative vs. Anion Radical Pathways" Wang, L.-C.; Jang, H.-Y.; Roh, Y.; Schultz, A. J.; Wang, X.; Lynch, V.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 9448.

"Anion Radical Chain Cycloaddition of Tethered Enones: Intramolecular Cyclobutanation and Diels-Alder Cycloaddition" Roh, Y.; Jang, H.-Y.; Bauld, N. L.; Krische, M. J. Org. Lett. 2002, 4, 611.

"Diastereoselective Metal Catalyzed [2+2]Cycloaddition of Tethered Enones" Baik, T.-G.; Wang, L.-C.; Luiz, A.-L.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 6716.

"Desymmetrization of Enone-Diones via Rhodium Catalyzed Catalytic Diastereo- and Enantioselective Tandem Conjugate Addition-Aldol Cyclization" Bocknack, B. M.; Wang, L.-C.; Krische, M. J. Proc. Nat. Acad. Sci. 2004, 101, 5421.

"Copper Catalyzed Tandem Conjugate Addition-Electrophilic Trapping: Ketones, Esters and Nitriles as Terminal Electrophiles" Agapiou, K.; Cauble, D. F.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4528.

"Diastereo- and Enantioselective Catalytic Carbometallative Aldol Cycloreduction: Tandem Conjugate Addition-Aldol Cyclization" Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.