Sherry R. Chemler

PhD

Sherry Chemler.

Sherry R. Chemler

PhD

Sherry R. Chemler

PhD

Research Interests

Organometallic chemistry, medicinal chemistry: New reaction development with earth-abundant copper and manganese catalysts, asymmetric catalysis, alkene difunctionalization reactions, natural product synthesis, synthesis and medicinal chemistry of nitrogen heterocycles.

Contact Information

618 Natural Sciences Complex

Buffalo NY, 14260

Phone: (716) 645-4225

Fax: (716) 645-6963

schemler@buffalo.edu

Education

  • NIH Postdoctoral Fellow, Memorial Sloan-Kettering Cancer Center, NY, NY, 1999-2002
  • PhD., Indiana University, 1999
  • BA, Boston University, 1994

Awards and Honors

  • ACS Administered PRFG (2004-2006)
  • Thieme Journal Prize (2008)
  • Chair-elect, Chair, Western New York ACS (2007-2009)
  • Organic Letters Advisory Board (2011-2016)
  • NIH SBCA Study Section Member (2013-2017)
  • ACS Cope Scholar Award (2017)
  • Science Advances Editorial Board (2016-)
  • UB Exceptional Scholar Award for Sustained Achievement (2018)

Specializations

Research in the Chemler group involves the development and study of new organic and organometallic reactions and the application of these reactions to the synthesis of valuable natural products and designed molecules with interesting molecular architecture and potent biological activity.

Research Summary

The Chemler group has recently discovered novel oxidative cyclization chemistry enabled by relatively inexpensive and non-toxic copper salts. In this context, the generality, mechanism and application of the copper promoted/catalyzed intramolecular carboamination, diamination and aminooxygenation of unactivated olefins are being explored. The efficiency of these methods in the synthesis of medicinally relevant nitrogen heterocycles is underway.

Selected Recent Publications

  • E. S. Sherman, S. R. Chemler,* T. B. Tan and O. Gerlits (2004). “Copper(II) Acetate Promoted Oxidative Cyclization of Arylsulfonyl-o-allylanilines,” Org. Lett. 10, 1573-1575.
  • M. R. Manzoni, T. P. Zabawa, D. Kasi and S. R. Chemler* (2004). “Palladium(II) Catalyzed Intramolecular Aminobromination and Aminochlorination of Olefins,” Organometallics 23, 5618-5621.
  • Y. Wu, K. Zu, J. Ni, S. Yeh, D. Kasi, N. S. James, S. R. Chemler and C. Ip* (2004). “Cellular and Molecular Effects of alpha-Tocopheryloxybutyrate: Lessons for the Design of Vitamin E Analog for Cancer Prevention,” Anticancer Research, 24, 3795-3802.
  • T. P. Zabawa; D. Kasi; S. R. Chemler,* (2005) “Copper(II) Acetate Promoted Intramolecular Diamination of Unactivated Olefins,” J. Am. Chem. Soc., 127, 11250-11251.
  • W. Zeng and S. R. Chemler* (2007) “Copper(II)-Catalyzed Enantioselective Intramolecular Carboamination of Alkenes,” J. Am. Chem. Soc. 129, 12948-12949.
  • P. H. Fuller, J.-W. Kim, S. R. Chemler* (2008) “Copper catalyzed enantioselective intramolecular aminooxygenation of alkenes,” J. Am. Chem. Soc. 130, 17638-17639.
  • J. Ni; T. Mai; S.-T. Pang, I. Haque, K. Huang, M. A. DiMaggio; S. Xie; N. S. James; D. Kasi; S. R. Chemler* and S. Yeh,* (2009) “Novel Vitamin E Ether Analog Inhibits Prostate Cancer Cell Growth In Vitro and In Vivo,” Clin. Cancer Res. 15, 898-906.
  • M. C. Paderes, L. Belding, B. Fanovic, T. Dudding,* J. B. Keister* and S. R. Chemler* (2012), “Evidence for Alkene Cis-Aminocupration, an Aminooxygenation Case Study: Kinetics, EPR Spectroscopy and DFT Calculations,” Chem. Eur. J. 18, 1711-1726.
  • T. W. Liwosz, S. R. Chemler* (2012), “Copper-Catalyzed Enantioselective Intramolecular Alkene Amination / Intermolecular Heck-type Coupling Cascade,” J. Am. Chem. Soc. 134, 2020-2023.
  • M. T. Bovino and S. R. Chemler* (2012), “Catalytic Enantioselective Alkene Aminohalogenation / Cyclization Involving Atom Transfer,” Angew. Chem. Int. Ed. 51, 3923-3927.
  • S. R. Chemler (2013) “Copper’s Contribution to Amination Catalysis,” Science, 341, 624-626.
  • T. W. Liwosz and S. R. Chemler* (2013), “Copper-Catalyzed Oxidative Heck Reactions between Alkyltrifluoroboratesand Vinyl Arenes,” Organic Letters (ACS), 15, 3034-3037. http://pubs.acs.org/doi/pdf/10.1021/ol401220b
  • T. W. Liwosz and S. R. Chemler* (2013), “Copper-Catalyzed Oxidative Amination and Allylic Amination of Alkenes,” Chemistry: A European Journal (Wiley-Blackwell), 19, 12771.
  • L. Belding, S. R. Chemler, T. Dudding* (2013), “A Computational Study of the Copper(II)-Catalyzed Enantioselective Intramolecular Aminooxygenation of Alkenes,” J. Org. Chem. 78, 10288.
  • B. W. Turnpenny and S. R. Chemler* (2014), “Copper-Catalyzed Alkene Diamination: Synthesis of Chiral 2-Aminomethylindolines and Pyrrolidines,” Chem. Sci. 5, 1786.
  • M. T. Bovino, T. W. Liwosz, N. E. Kendel, Y. Miller, N. Tyminska, E. Zurek,* S. R. Chemler,* (2014), “Enantioselective Copper-Catalyzed Carboetherification of Unactivated Alkenes,” Angew. Chem. Int. Ed., 53, 6383.
  • T. W. Liwosz, S. R. Chemler* (2015), “Copper-Catalyzed Synthesis of N-Aryl and N-Sulfonyl Indoles from 2-Vinylanilines with O2 as Terminal Oxidant and TEMPO as Co-Catalyst,” Synlett, 26, 335-339. (Invited for cluster issue on earth abundant metals in catalysis.)
  • S. Karyakarte, F. C. Sequeira, G. H. Zibreg, G. Huang, J. P. Matthew, M. M. M. Ferreira and S. R. Chemler* (2015), “Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination,” Tetrahedron Lett. 56, 3686. (Invited for memorial issue for Harry Wasserman.)
  • B. J. Casavant, Z. M. Khoder, I. A. Berhane, S. R. Chemler* (2015), “Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters,” Org. Lett. 17, 5958.
  • C. Um, Sherry R. Chemler* (2016), “Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium beta-Aminoethyl Trifluoroborates,” Org. Lett. 18, 2515.
  • Z. M. Khoder, C. E. Wong, S. R. Chemler (2017), "Stereoselective Synthesis of Isoxazolidinones Via Copper-Catalyzed Alkene Diamination," ACS Catalysis 7, 4775-4779.
  • T. Wdowik, S. R. Chemler (2017), "Direct Synthesis of 2-Formylpyrrolidines, 2-Pyrrolidinones and 2-Dihydrofuranones Via Aerobic Copper-Catalyzed Aminooxygenation and Dioxygenation of 4-Pentenylsulfonamides and 4-Pentenylalcohols," J. Am. Chem. Soc. 139, 9515-9518.
  • J. M. Shikora, S. R. Chemler (2018), "Synthesis of Benzylamines via Copper-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Phenols to N-Sulfonyl Aldimines," Org. Lett. 20, 2133-2137.
  • S. D. Karyakarte, C. Um, I. A. Berhane, S. R. Chemler (2018), "Synthesis of Spirocyclic Ethers by Enantioselective Copper-Catalyzed Carboetherification of Alkenols," Angew. Chem. Int. Ed., 57, 12921-12924.
  • D. Chen, S. R. Chemler (2018), "Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols,” 20, 6453-6456.