Asymmetric Catalysis, Organometallic Chemistry & Organic Synthesis

 

 

group retreat 2016 2

 

Recent Research Highlights

Bischoff, A. J.; Nelson, B. M.; Niemeyer, Z. L.; Sigman, M. S.; Movassaghi, M."Quantitative Modeling of Bis(pyridine)silver(I) Permanganate Oxidation of Hydantoin Derivatives: Guidelines for Predicting the Site of Oxidation in Complex Substrates" J. Am. Chem. Soc.2017DOI: 10.1021/jacs.7b09541

amanda


Engl, P. S.; Santiago, C. B.; Gordon, C. P.; Liao, W.-C.; Fedorov, A.; Copéret, C.; Sigman, M. S.; Togni, A. "Exploiting and Understanding the Selectivity of Ru-N-Heterocyclic Carbene Metathesis Catalysts for the Ethenolysis of Cyclic Olefins to α,ω-Dienes" J. Am. Chem. Soc.  2017, 139, 13117.

Togni


Orlandi, M.; Hilton, M. J.; Yamamoto, E.; Toste, F. D.; Sigman, M. S. "Mechanistic Investigations of the Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Benzyl Acrylates" J. Am. Chem. Soc.2017, 139, 12688.

manuel


Niemeyer, Z. L.; Pindi, S.; Khrakovsky, D. A.; Kuzniewski, C. N.; Hong, C. M.; Joyce, L. A.; Sigman, M. S.; Toste, F. D. "Parameterization of Acyclic Diaminocarbene Ligands Applied to a Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization" J. Am. Chem. Soc.2017, 139, 12943.

zach


 Keylor, M. H.; Niemeyer, Z. L.; Sigman, M. S.; Tan, K. L."Inverting Conventional Chemoselectivity in Pd-Catalyzed Amine Arylations with Multiply Halogenated Pyridines" J. Am. Chem. Soc.2017, 139, 10613.

zack


 Guo, J.-Y.; Minko, Y.; Santiago, C. B.; Sigman, M. S. "Developing Comprehensive Computational Parameter Sets To Describe the Performance of Pyridine-Oxazoline and Related Ligands" ACS Catal. 2017, 7, 4144.

iris


Mack, J. B. C.; Gipson, J. D.; Du Bois, J.; Sigman, M. S. "Ruthenium-Catalyzed C–H Hydroxylation in Aqueous Acid Enables Selective Functionalization of Amine Derivatives" J. Am. Chem. Soc.2017 139, 9503.

Mack


Plata, R. E.; Hill, D. E.; Haines, B. E.; Musaev, D. G.; Chu, L.; Hickey, D. P.; Sigman, M. S.; Yu, J.-Q.; Blackmond, D. G. "A Role for Pd(IV) in Catalytic Enantioselective C–H Functionalization with Monoprotected Amino Acid Ligands under Mild Conditions" J. Am. Chem. Soc.2017, 139, 9238.

Blackmond


 Orlandi, M.; Coelho, J. A. S.; Hilton, M. J.; Toste, F. D.; Sigman, M. S. "Parametrization of Non-covalent Interactions for Transition State Interrogation Applied to Asymmetric Catalysis" J. Am. Chem. Soc.2017, 139, 6803.

Manuel


Christian, A. H.; Niemeyer, Z. L.; Sigman, M. S.; Toste, F. D. "Uncovering Subtle Ligand Effects of Phosphines Using Gold(I) Catalysis" ACS Catal. 2017, 3973.

gold


 Avila, C. M.; Patel, J. S.; Reddi, Y.; Saito, M.; Nelson, H. M.; Shunatona, H. P.; Sigman, M. S.; Sunoj, R. B.; Toste, F. D. "Enantioselective Heck–Matsuda Arylations through Chiral Anion Phase-Transfer of Aryl Diazonium Salts" Angew. Chem. Int. Ed.2017, 56. 5806.

toste-ang


 Chen, Z.-M.; Nervig, C. S.; DeLuca, R. J.; Sigman, M. S.* "Palladium-Catalyzed Enantioselective Redox-Relay Heck Alkynylation of Alkenols to Access Propargylic Stereocenters” Angew. Chem. Int. Ed.2017, 56, 1.

alkynylation


 

B. P. Woods, M. Orlandi, C.-Y. Huang, M. S. Sigman, A. G. Doyle, J. Am. Chem. Soc. 2017 DOI: 10.1021/jacs.7b03448

doyle


 F. D. Toste, M. S. Sigman, S. J. Miller"Pursuit of Noncovalent Interactions for Strategic Site-Selective Catalysis" Acc. Chem. Res. 2017, 50, 609.

accounts


  A. J. Neel, M. J. Hilton, M. S. Sigman, F. D. Toste "Exploiting non-covalent π interactions for catalyst design" Nature 2017, 543, 637.

nature rev


 Sevov, C. S.; Hickey, D. P.; Cook, M. E.; Robinson, S. G.; Barnett, S.; Minteer, S. D.*; Sigman, M. S.*; Sanford, M. S.* " Physical Organic Approach to Persistent, Cyclable, Low-Potential Electrolytes for Flow Battery Applications,"J. Am. Chem. Soc2017139, 2924.

Battery


Zhang, C.; Tutkowski, B.; DeLuca, R. J.; Joyce, L. A.  WiestO.; Sigman, M. S.* "Palladium-catalyzed enantioselective Heck alkenylation of trisubstituted allylic alkenols: a redox-relay strategy to construct vicinal stereocenters," Chem. Sci.  20178, 2277.

Chun

 


 

Related Websites

Department of Chemistry

Seminar Schedule

University of Utah

Center for Stereoselective Functionalization Logo

Contact Information

Matthew S. Sigman
315 So. 1400 E. Rm. 4253A
Salt Lake City, UT 84112
sigman@chem.utah.edu
Office: (801) 585-0774

Group News

The Sigman group's work in collaboration with the Doyle group was highlighted as Synfact of the Month!

Nick Race's report in JACS was featured in Organic Chemistry Highlights .

The Sigman group's work in collaboration with the Sanford group on redox-active electrolytes for flow batteries was featured on the cover of JACS and was highlighted in C&E News.

The Sigman group's work on non-covalent interactions was discussed in Forbes.

Nick Race's report in JACS was highlighted in Synfacts.

Harsh Patel's report in JACS was highlighted in Synfacts.

Matthew Sigman is featured in C&E News for receiving the ACS award for creative work in synthetic organic chemistry.

Nick Race's report in JACS was highlighted in C&E News

Celine Santiago’s report in JACS was highlighted in JACS Spotlights. 

Anat Milo’s report in JACS was highlighted in JACS Spotlights. 

David Hickey and David Schiedler's report in JACS was highlighted in JACS Spotlights. 

Tian-Sheng Mei and Harsh Patel's report in Nature was highlighted:News and Views: Morken, J. P. “Catalysis Marches On,” Nature 2014, 508, 324-325;Highlighted:Chem. & Eng. News 2014, 92 (15), 6.
 
Anat Milo's report in Nature was featured on the University of Utah website, in C&E News, and on the following science websites: Science360, Azom.com, Eureka! Science News, Science 2.0, Laboratory Equipment, Science Codex, EurekAlert, Phys.Org, Newswise, Chemicals Technology, Daily News.
 
The Sigman group put together a short video about why they love chemistry!
Last Updated: 10/24/17