Sherry R. Chemler
Office: 618 Natural Sciences Complex
Phone: (716) 645-4225
Fax: (716) 645-6963
Lab website: http://www.acsu.buffalo.edu/~schemler/
Information on the Chemler Research Group
Information on the Chemler Research Group 2
- NIH Postdoctoral Fellow, Memorial Sloan-Kettering Cancer Center, NY, NY (1999-2002)
- Ph.D., Indiana University (1999)
- B. A., Boston University (1994)
- ACS Administered PRFG (2004-2006)
- Thieme Journal Prize (2008)
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.
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:
F. C. Sequiera, B. W. Turnpenny and S. R. Chemler (2010), “Copper-Promoted and Catalyzed Intermolecular Diamination of Alkenes,” Angew. Chemie. Int. Ed. 49, 6365-6368.
- L. Miao, I. Haque, M. R. Manzoni, W. S. Tham and S. R. Chemler (2010), “Diastereo- and Enantioselective Copper-Catalyzed Intramolecular Carboamination of Alkenes for the Synthesis of Hexahydro-1H-benz[f]indoles,” Org. Lett. 12, 4739-4741.
- M. Paderes and S. R. Chemler (2009), “Diastereoselective Pyrrolidine Synthesis via Copper Promoted Intramolecular Aminooxygenation of Alkenes; Formal Synthesis of (+)-Monomurine,” Org. Lett. 11, 1915-1918.
- E. S. Sherman and S. R. Chemler (2009), “Copper(II)-Catalyzed Aminooxygenation and Carboamination of N-Aryl-2-allylanilines,” Adv. Synth. Catal. 351, 467-471.
- 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.
- P. H. Fuller, J.-W. Kim and S. R. Chemler (2008), “Copper Catalyzed Enantioselective Intramolecular Aminooxygenation of Alkenes,” J. Am. Chem. Soc. 130, 17638-17639.
- W. Zeng and S. R. Chemler (2008), “Total Synthesis of (S)-(+)-Tylophorine Via Enantioselective Intramolecular Alkene Carboamination,” J. Org. Chem. 73, 6045-6047.
- P. H. Fuller and S. R. Chemler (2007), “Copper(II) Carboxylate Promoted Intramolecular Carboamination of Alkenes for the Synthesis of Polycyclic Lactams,” Org. Lett. 9, 5477-5480.
- W. Zeng and S. R. Chemler (2007), “Copper(II)-Catalyzed Enantioselective Intramolecular Carboamination of Alkenes,” J. Am. Chem. Soc. 129, 12948-12949.
- T. P. Zabawa and S. R. Chemler (2007), “Copper(II) Carboxylate Promoted Intramolecular Diamination of Unactivated Alkenes for the Synthesis of Cyclic Vicinal Diamines: Diastereoselectivity and Expanded Substrate Scope,” Org. Lett. 9, 2035-2038.
- E. S. Sherman, P. H. Fuller, D. Kasi, S. R. Chemler (2007), “Pyrrolidine and Piperdine Formation Via Copper(II) Carboxylate Promoted Intramolecular Carboamination of Unactivated Olefins: Diastereoselectivity and Mechanism,” J. Org. Chem. 72, 3896-3905.
- E. Cheng, J. Ni, Y. Yin, C. C. Lin, P. Chang, N. S. James, S. R. Chemler, S. Yeh (2007), “Alpha-Vitamin E Derivative, RRR-alpha-Tocopheryloxybutyric Acid Inhibits the Proliferation of Prostate Cancer Cells,” Asian J. Andrology, 9, 31.
- 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.
- 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.
- M. R. Manzoni, T. P. Zabawa, D. Kasi and S. R. Chemler (2004), “Palladium(II) Catalyzed Intramolecular Aminobromination and Aminochlorination of Olefins,” Organometallics, 5618-5621.
- 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.
- S. R. Chemler, D. Trauner and S. J. Danishefsky (2001), “The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study and Applications in Natural Product Synthesis,” Angew. Chem, Int. Ed. 40, 4544-4568.
- S. R. Chemler and P. H. Fuller (2007), “Heterocycle Synthesis by Copper Facilitated Additions of Amines to Alkenes, Alkynes and Arenes,” Chemical Society Reviews, invited review, 36, 1153-1160.
- S. R. Chemler (2009), “Phenanthroindolizidines and Phenanthroquinolizidines: Promising Alkaloids for Anti-Cancer Therapy,” invited review, Current Bioactive Compounds, 5, 2-19.
- S. R. Chemler (2009), “The Enantioselective Intramolecular Aminative Functionalization of Unactivated Alkenes, Dienes, Allenes and Alkynes for the Synthesis of Chiral Nitrogen Heterocycles,” invited review, Organic and Biomolecular Chemistry, 7, 3009-3019.
- S. R. Chemler (2011), “Evolution of Copper(II) as a New Alkene Amination Promoter and Catalyst,” J. Organomet. Chem., 696, 150-158.
- S. R. Chemler and W. R. Roush (2001), “Recent Applications of the Allylation Reaction to the Synthesis of Natural Products,” Chap. 11 in Modern Carbonyl Chemistry, J. Otera, Ed., Wiley-VCH: Weinheim.