Abstract

Catalytic C-C bond formation lies at the core of synthetic organic chemistry. The capture of hydrogenation intermediates represents a mechanistically and strategically novel paradigm for the development of catalytic C-C bond formations. In the proposed funding period, the concepts underlying this new pattern of reactivity will be uncovered in an effort to expand this emergent reaction type, with the goal of enabling useful alternatives to classical carbanion and carbonyl addition chemistry. ? ?

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
1R01GM069445-01A2
Application #
6913940
Study Section
Medicinal Chemistry Study Section (MCHA)
Program Officer
Schwab, John M
Project Start
2005-03-15
Project End
2009-02-28
Budget Start
2005-03-15
Budget End
2006-02-28
Support Year
1
Fiscal Year
2005
Total Cost
$243,595
Indirect Cost

  Institution

Name
University of Texas Austin
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
170230239
City
Austin
State
TX
Country
United States
Zip Code
78712

  Publications

Cabrera, James M; Tauber, Johannes; Zhang, Wandi et al. (2018) Selection between Diastereomeric Kinetic vs Thermodynamic Carbonyl Binding Modes Enables Enantioselective Iridium-Catalyzed anti-(?-Aryl)allylation of Aqueous Fluoral Hydrate and Difluoroacetaldehyde Ethyl Hemiacetal. J Am Chem Soc 140:9392-9395
Meza, Arismel Tena; Wurm, Thomas; Smith, Lewis et al. (2018) Amphiphilic ?-Allyliridium C,O-Benzoates Enable Regio- and Enantioselective Amination of Branched Allylic Acetates Bearing Linear Alkyl Groups. J Am Chem Soc 140:1275-1279
Kim, Seung Wook; Wurm, Thomas; Brito, Gilmar A et al. (2018) Hydroamination versus Allylic Amination in Iridium-Catalyzed Reactions of Allylic Acetates with Amines: 1,3-Aminoalcohols via Ester-Directed Regioselectivity. J Am Chem Soc 140:9087-9090
Holmes, Michael; Schwartz, Leyah A; Krische, Michael J (2018) Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines. Chem Rev 118:6026-6052
Cabrera, James M; Tauber, Johannes; Krische, Michael J (2018) Enantioselective Iridium-Catalyzed Phthalide Formation through Internal Redox Allylation of Phthalaldehydes. Angew Chem Int Ed Engl 57:1390-1393
Brito, Gilmar A; Della-Felice, Franco; Luo, Guoshun et al. (2018) Catalytic Enantioselective Allylations of Acetylenic Aldehydes via 2-Propanol-Mediated Reductive Coupling. Org Lett 20:4144-4147
Roane, James; Holmes, Michael; Krische, Michael J (2017) Reductive C-C Coupling via Hydrogenation and Transfer Hydrogenation: Departure from Stoichiometric Metals in Carbonyl Addition. Curr Opin Green Sustain Chem 7:1-5
Kim, Seung Wook; Lee, Wonchul; Krische, Michael J (2017) Asymmetric Allylation of Glycidols Mediated by Allyl Acetate via Iridium-Catalyzed Hydrogen Transfer. Org Lett 19:1252-1254
Roane, James; Wippich, Julian; Ramgren, Stephen D et al. (2017) Synthesis of the C(1)-C(13) Fragment of Leiodermatolide via Hydrogen-Mediated C-C Bond Formation. Org Lett 19:6634-6637
Luong, Tom; Chen, Shujie; Qu, Ke et al. (2017) Ruthenium(0)-Catalyzed C-C Coupling of Alkynes and 3-Hydroxy-2-oxindoles: Direct C-H Vinylation of Alcohols. Org Lett 19:966-968

Showing the most recent 10 out of 125 publications