Glenn Sammis

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Glenn Sammis

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Research and Teaching Interests

Our research focuses on the development of new methods for the syntheses of architecturally complex natural products. This encompasses the development of new methods for the fluorination of alkyl and aryl radicals, the use of oxygen- and nitrogen-centered radicals for the synthesis of heterocycles, organometallic reagents for the development of new bond construction techniques, the enantioselective synthesis of building blocks for total synthesis, and the development and evaluation of proposed biogenetic pathways through biomimetic synthesis. Central to efficient methods development is a fundamental understanding of reactivity and reaction mechanisms.

Recent highlights of our research are:

  • Fluorine Atom Transfer to Alkyl Radicals. The development of new synthetic technologies for the selective fluorination of organic compounds has increased with the escalating importance of fluorine-containing pharmaceuticals. Traditional methods potentially applicable to drug synthesis rely on the use of ionic forms of fluorine (F– or F+). Radical methods, while potentially attractive as a complementary approach, are hindered by a paucity of safe sources of atomic fluorine (F·). We have developed a new approach to alkyl fluorination that utilizes the reagent N-fluorobenzenesulfonimide as a fluorine transfer agent to alkyl radicals (J. Am. Chem. Soc. 2012, 134, 4026-4029). This approach is successful for a broad range of alkyl radicals, including primary, secondary, tertiary, benzylic, and heteroatom stabilized radicals. Furthermore, calculations reveal that Selectfluor®, and related ionic reagents, are likely candidates for further expansion of this approach to polar reaction media. The use of these reagents in alkyl radical fluorination has the potential to enable powerful new transformations that otherwise would take multiple synthetic steps.
    Fluorine
  • Radical Relay Cyclizations. We have developed an efficient method for the rapid construction of bioactive carbo- and heterocycles using radical relay cyclization initiated by alkoxy radicals. This new method allows for the rapid increase in molecular complexity from simple starting materials though the conversion of unactivated C-H bonds into reactive intermediates. The cyclizations are effective for the synthesis of a wide range of cyclopentane, pyrrolidine, tetrahydropyran, and tetrahydrofurans derivatives.
    Radical relay cyclization

We are currently further exploring this new synthetic method in the total synthesis of both (–)-lepadiformine A and (–)-amphidinolide K. Each synthesis involves synthesizing complex heterocyclic fragments by using sequential or cascade reactions in which complexity is rapidly achieved from simple linear precursors. We are also currently developing new, non-radical synthetic methods for the syntheses of heterocycles.
Targets

Contact

Real name: 
Email: 
Office Room Number(s): 
349 Chem/Phys
Office Phone Number: 
604-827-4080
Lab Phone: 
604-827-4442
Fax Number: 
604-822-2847

Curriculum Vitae

B.S. (honors), Stanford University (1999); Ph.D., Harvard University (Eric. N. Jacobsen, 2004); National Institutes of Health Postdoctoral Fellow, Princeton University (Erik. J. Sorensen, 2004-2006)

Publications

2014

Campbell, N. E. ; Sammis, G. M. Single-Electron/pericyclic Cascade For The Synthesis Of Dienes. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 2014, 53, 6228-6231.
Rueda-Becerril, M. ; Mahe, O. ; Drouin, M. ; Majewski, M. B. ; West, J. G. ; Wolf, M. O. ; Sammis, G. M. ; Paquin, J. - F. Direct C-F Bond Formation Using Photoredox Catalysis. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 2014, 136, 2637-2641.

2013

2012

Zhai, H. ; Miller, J. ; Sammis, G. M. First Enantioselective Syntheses Of The Dopamine D1 And D2 Receptor Modulators, (+)- And (-)-Govadine. Bioorganic & Medicinal Chemistry Letters 2012, 22, 1557 - 1559.
Hadidi, S. ; Antignano, F. ; Hughes, M. R. ; Wang, S. K. H. ; Snyder, K. ; Sammis, G. M. ; Kerr, W. G. ; McNagny, K. M. ; Zaph, C. Myeloid Cell-Specific Expression Of Ship1 Regulates Il-12 Production And Immunity To Helminth Infection. MUCOSAL IMMUNOLOGY 2012, 5, 535-543.
Rueda-Becerril, M. ; Sazepin, C. Chatalova; Leung, J. C. T. ; Okbinoglu, T. ; Kennepohl, P. ; Paquin, J. - F. ; Sammis, G. M. Fluorine Transfer To Alkyl Radicals. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 2012, 134, 4026-4029.
Leung, J. C. T. ; Chatalova-Sazepin, C. ; West, J. G. ; Rueda-Becerril, M. ; Paquin, J. - F. ; Sammis, G. M. Photo-Fluorodecarboxylation Of 2-Aryloxy And 2-Aryl Carboxylic Acids. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 2012, 51, 10804-10807.

2011

Zlotorzynska, M. ; Sammis, G. M. Photoinduced Electron-Transfer-Promoted Redox Fragmentation Of N -Alkoxyphthalimides. Organic Letters 2011, 13, 6264 - 6267.
Rueda-Becerril, M. ; Leung, J. C. T. ; Dunbar, C. R. ; Sammis, G. M. Alkoxy Radical Cyclizations Onto Silyl Enol Ethers Relative To Alkene Cyclization, Hydrogen Atom Transfer, And Fragmentation Reactions. The Journal of Organic Chemistry 2011, 76, 7720 - 7729.
Xie, H. ; Sammis, G. M. ; Flamme, E. M. ; Kraml, C. M. ; Sorensen, E. J. The Catalytic Asymmetric Diels-Alder Reactions And Post-Cycloaddition Reductive Transpositions Of 1-Hydrazinodienes. Chemistry - A European Journal 2011, 17, 11131 - 11134.

2010

Zlotorzynska, M. ; Zhai, H. ; Sammis, G. Construction Of Protected Hydroxylated Pyrrolidines Using Nitrogen-Centered Radical Cyclizations. In; American Chemical Society, 2010; p. ORGN-531.
Zlotorzynska, M. ; Zhai, H. - M. ; Sammis, G. M. Unique Diastereoselectivity Trends In Aminyl Radical Cyclizations Onto Silyl Enol Ethers. Journal of Organic Chemistry 2010, 75, 864 - 872.
Zhai, H. ; Wickenden, J. ; Sammis, G. M. Cyclizations Of Aminyl Radicals Generated From Substoichiometric Stannane. Synlett 2010, 2010, 3035 - 3038.

2009

Zhai, H. M. ; Zlotorzynska, M. ; Sammis, G. Construction Of Protected Hydroxylated Pyrrolidines Using Nitrogen-Centered Radical Cyclizations. Chemical Communications 2009, 5716-5718.
Zhu, H. ; Wickenden, J. G. ; Campbell, N. E. ; Leung, J. C. T. ; Johnson, K. M. ; Sammis, G. M. Construction Of Carbo- And Heterocycles Using Radical Relay Cyclizations Initiated By Alkoxy Radicals. Organic Letters 2009, 11, 2019-2022.
Zhai, H. ; Zlotorzynska, M. ; Sammis, G. M. Construction Of Protected Hydroxylated Pyrrolidines Using Nitrogen-Centered Radical Cyclizations. Chemical Communications 2009, 5716.

2008

Zlotorzynska, M. ; Zhai, H. ; Sammis, G. M. Chemoselective Oxygen-Centered Radical Cyclizations Onto Silyl Enol Ethers. Organic Letters 2008, 10, 5083-5086.

2005

Sammis, G. M. ; Flamme, E. M. ; Xie, H. ; Ho, D. M. ; Sorensen, E. J. Design, Synthesis, And Reactivity Of 1-Hydrazinodienes For Use In Organic Synthesis. Journal of the American Chemical Society 2005, 127, 8612 - 8613.

2004

Sammis, G. M. ; Danjo, H. ; Jacobsen, E. N. Cooperative Dual Catalysis:  Application To The Highly Enantioselective Conjugate Cyanation Of Unsaturated Imides. Journal of the American Chemical Society 2004, 126, 9928 - 9929.
Sorensen, E. J. ; Sammis, G. M. Chemistry: Enhanced: A Dash Of Proline Makes Things Sweet. Science 2004, 305, 1725 - 1726.

2003

Sammis, G. M. ; Jacobsen, E. N. Highly Enantioselective, Catalytic Conjugate Addition Of Cyanide To Alpha,beta-Unsaturated Imides. Journal of the American Chemical Society 2003, 125, 4442-3.

2000

Millward, D. B. ; Sammis, G. M. ; Waymouth, R. M. Ring-Opening Reactions Of Oxabicyclic Alkene Compounds:  Enantioselective Hydride And Ethyl Additions Catalyzed By Group 4 Metals. The Journal of Organic Chemistry 2000, 65, 3902 - 3909.

Research Projects