2000 - 2009

H2-MEDIATED C-C COUPLING (& RELATED WORK)

"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.

http://pubs.acs.org/doi/abs/10.1021/ja904124b

"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.

http://onlinelibrary.wiley.com/doi/10.1002/ange.200902328/full

"Direct Prenylation of Aromatic and α,β-Unsaturated Carboxamides via Iridium Catalyzed C-H Oxidative Addition-Allene Insertion," Zhang, Y. J.; Skucas, E.; Krische, M. J. Org. Lett.2009, 11, 4248.

"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.

http://pubs.acs.org/doi/abs/10.1021/ol901136w

"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.

http://onlinelibrary.wiley.com/doi/10.1002/anie.200901648/abstract?systemMessage=Wiley+Online+Library+will+be+disrupted+14+May+from+10-12+BST+for+monthly+maintenance

"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.

http://pubs.acs.org/doi/abs/10.1021/ja902437k

"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.

http://pubs.acs.org/doi/abs/10.1021/ja900827p

"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.

http://pubs.acs.org/doi/abs/10.1021/ja809456u

"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.

http://pubs.acs.org/doi/abs/10.1021/ja808857w

"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.

http://www.sciencedirect.com/science/article/pii/S0040402009004633

"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.; Nagi, M. -Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14891.

http://pubs.acs.org/doi/abs/10.1021/ja805722e

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

http://pubs.acs.org/doi/abs/10.1021/ja805356j

"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.

http://pubs.acs.org/doi/abs/10.1021/ja805056g

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

http://pubs.acs.org/doi/abs/10.1021/ol8018874

"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.

http://pubs.acs.org/doi/abs/10.1021/ol800836v

"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.

http://onlinelibrary.wiley.com/doi/10.1002/anie.200801359/abstract?systemMessage=Wiley+Online+Library+will+be+disrupted+14+May+from+10-12+BST+for+monthly+maintenance

"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.

http://pubs.acs.org/doi/abs/10.1021/ja802001b

"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.

http://pubs.acs.org/doi/abs/10.1021/ja801213x

"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.

http://pubs.acs.org/doi/abs/10.1021/ja710862u

"Iridium Catalyzed C-C Coupling 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.

http://pubs.acs.org/doi/abs/10.1021/ol800159w

"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.

http://pubs.acs.org/doi/abs/10.1021/ja077389b

"Enantioselective 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.

http://pubs.acs.org/doi/abs/10.1021/ja075438e

"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.

http://pubs.acs.org/doi/abs/10.1021/ja075971u

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

http://pubs.acs.org/doi/abs/10.1021/ol7015548

"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.

http://pubs.acs.org/doi/abs/10.1021/ja073018j

"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.

http://pubs.acs.org/doi/abs/10.1021/ja0715896

"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.

http://pubs.acs.org/doi/abs/10.1021/ja0670815

"Asymmetric Induction in Hydrogen-Mediated Reductive Aldol Additions to α-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.

http://pubs.acs.org/doi/abs/10.1021/ja066198q

"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.

http://pubs.acs.org/doi/abs/10.1021/ja0673027

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

http://pubs.acs.org/doi/abs/10.1021/ja0664786

"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.

http://onlinelibrary.wiley.com/doi/10.1002/anie.200602377/abstract;jsessionid=D744A653B817ECCEDBF9A927071D04FD.d01t01?systemMessage=Wiley+Online+Library+will+be+disrupted+14+May+from+10-12+BST+for+monthly+maintenance

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

http://pubs.acs.org/doi/abs/10.1021/ol0624023

"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.

http://pubs.acs.org/doi/abs/10.1021/ja0637954

"α-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.

http://pubs.acs.org/doi/abs/10.1021/ol061485k

"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.

http://pubs.acs.org/doi/abs/10.1021/ol052976s

"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.

http://pubs.acs.org/doi/abs/10.1021/ol052859x

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

http://pubs.acs.org/doi/abs/10.1021/ja056474l

"Hydrogen-Mediated Reductive Coupling of Conjugated Alkynes with Ethyl (N-sulfinyl)iminoacetates: Diastereoselective Synthesis of Unnatural α-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.

http://pubs.acs.org/doi/abs/10.1021/ja051104i

"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.

http://pubs.acs.org/doi/abs/10.1021/ja042645v

"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.

http://pubs.acs.org/doi/abs/10.1021/ja048498i

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

http://pubs.acs.org/doi/abs/10.1021/ja0316566

"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.

http://pubs.acs.org/doi/abs/10.1021/ol030136c

"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.

http://pubs.acs.org/doi/abs/10.1021/jo030310a

"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.

http://pubs.acs.org/doi/abs/10.1021/ja030415v

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

http://pubs.acs.org/doi/abs/10.1021/ol0300219

"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.

http://pubs.acs.org/doi/abs/10.1021/ja021163l

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