Asymmetric Catalysis, Organometallic Chemistry & Organic Synthesis

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Recent Research Highlights

Yuan, Q.; Sigman, M. S. "Palladium-Catalyzed Enantioselective Relay Heck Arylation of Enelactams: Accessing α,β-Unsaturated δ-Lactams" J. Am. Chem. Soc.2018 ASAP DOI: 10.1021/jacs.8b02752

q pub

Patel, H. H.; Prater, M. B.; Squire, S. O.; Sigman, M.S.* "Formation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers"  J. Am. Chem. Soc. ASAP DOI: 10.1021/jacs.8b02751

harsh pub

Crawford, J. M.; Stone, E. A.; Metrano, A. J.; Miller, S. J.; Sigman, M. S. "Parameterization and Analysis of Peptide-Based Catalysts for the Atroposelective Bromination of 3‐Arylquinazolin-4(3H)‐ones" J. Am. Chem. Soc.2018, 140, 868.


Biswas, S.; Kubota, K.; Orlandi, M.; Turberg, M.; Miles, D. H.; Sigman, M. S.; Toste, F. D. "Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis"Angew. Chem. Int. Ed.DOI: 10.1002/anie.201711277


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


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.


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.


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.


 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.


 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.


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.


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.


 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.


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.


 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.


 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.



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


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


  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.


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.




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Contact Information

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

Group News

Congratulations to Nicholas Race for becoming the newest faculty member at Univerisy of Minnesota in the department of Chemistry! 

Congratulations to Rachel Vaden for her new position at Pfizer as a  research scientist in the cancer drug discovery group!

Congratulations to Elizabeth Bess for becoming the newest faculty member at UC-Irivine  in Chemical Biology!

Yoonsu Park's work in collaboration with Zach Niemeyer from the Sigman lab  was featured on the cover of Organometallics.

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,, 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: 5/16/18