Publications

2014

T. W. Liwosz, S. R. Chemler (2014), "Copper-Catalyzed Synthesis of N-Aryl and N-Sulfonyl Indoles from 2-Vinylanilines with O2 as Terminal Oxidant and TEMPO as Co-Catalyst," Synlett, in press.

B. J. Casavant, A. S. Hosseini, S. R. Chemler (2014), "6-Azabicyclo[3.2.1]octanes Via Copper-Catalyzed Enantioselective Alkene Carboamination," Adv. Syn. Cat. 356, 2697.

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.

B. W. Turnpenny, S. R. Chemler (2014), "Copper-Catalyzed Alkene Diamination: Synthesis of Chiral 2-Aminomethylindolines and Pyrrolidines," Chem. Sci. 5, 1786.

2013

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.

S. R. Chemler (2013), "Copper's Contribution to Amination Catalysis," Science, 341, 624-626.

T. W. Liwosz, S. R. Chemler (2013), "Copper-Catalyzed Oxidative Amination and Allylic Amination of Alkenes," Chem.--Eur. J. 19. 12771.

T. W. Liwosz, S. R. Chemler (2013), "Copper-Catalyzed Oxidative Heck Reactions between Alkyltrifluoroborates and Vinyl Arenes," Org. Lett. 15, 3034-3037.

S. R. Chemler, M. T. Bovino (2013), "Catalytic Aminohalogenation of Alkenes and Alkynes," ACS Catalysis, 3, 1076-1091.

M. C. Paderes, J. B. Keister, S. R. Chemler (2013), "Mechanistic Analysis and Optimization of the Copper-Catalyzed Enantioselective Intramolecular Alkene Aminooxygenation," J. Org. Chem., 78, 506-515.

2012

S. R. Chemler, B. J. Casavant, (2012) "Copper(II)-Ethylhexanoate," e-Eros (invited contribution),  DOI: 10.1002/047084289X.

B. W. Turnpenny, K. L. Hyman, S. R. Chemler (2012) "Chiral Indoline Synthesis Via Enantioselective Intramolecular Copper-Catalyzed Alkene Hydroamination," Organometallics, 31, 7819-7822.

F. C. Sequiera, S. R. Chemler (2012) "Stereoselective Synthesis of Morpholines Via Copper(II)-Promoted Alkene Aminooxygenation," Org. Lett. 14, 4482-4485.

S. Karyakarte, T. P. Smith, S. R. Chemler (2012) "Stereoselective Isoxazolidine Formation Via Copper-Catalyzed Alkene Aminooxygenation," J. Org. Chem. 77, 7755-7760.

Y. Miller, L. Miao, A. Hosseini, S. R. Chemler (2012) "Copper-Catalyzed Intramolecular Alkene Carboetherification: Synthesis of Fused-Ring and Bridged-Ring Tetrahydrofurans," J. Am. Chem. Soc. 134, 12149-12156.

F. C. Sequeira, M. T. Bovino, A. J. Chipre, S. R. Chemler (2012) "Multigram Synthesis of a Chiral Substituted Indoline Via Copper-Catalyzed Alkene Aminooxygenation," Synthesis, 44, 1481-1484.

M. T. Bovino, S. R. Chemler (2012), "Atom Transfer as a New Solution for Catalytic Enantioselective Alkene Aminohalogenation / Cyclization," Angew. Chem. Int. Ed.  51, 3923-3927.

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. 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.

2011

 

M. C. Paderes and S. R. Chemler (2011), "Stereoselective Copper-Catalyzed Intramolecular Alkene Aminooxygenation: Effects of Substrate and Ligand Structure on Selectivity," Eur. J. Org. Chem. (Special Edition), 3679-3684. [Full Text PDF]

S. R. Chemler (2011), "Evolution of Copper(II) as a New Alkene Amination Promoter and Catalyst," J. Organomet. Chem. 696, 150-158. [Full Text PDF]

2010

L. Miao, I. Haque, M. R. Manzoni, W. S. Tham, 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. (Highlighted in Synfacts). [Full Text PDF]

F. C. Sequeira, B. W. Turnpenny, S. R. Chemler (2010), "Copper-Promoted and Copper-Catalyzed Intermolecular Alkene Diamination," Angew. Chem. Int. Ed. 49, 6365-6368. [Full Text PDF]

2009

M. C. 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. [Full Text PDF]

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.

S. R. Chemler (2009), "Phenanthroindolizidines and Phenanthroquinolizidines: Promising Alkalids for Anti-Cancer Therapy," Current Bioactive Compounds, 3, 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," Org. and Biomol. Chem. 7, 3009-3019.

2008

P. H. Fuller, J. W. Kim, S. R. Chemler (2008), "Copper Catalyzed Enantioselective Intramolecular Aminooxygenation of Alkenes," J. Am. Chem. Soc. 130, 17638-17639.

W. Zeng, S. R. Chemler (2008), "Total Synthesis of (S)-(+)-Tylophorine Via Enantioselective Intramolecular Alkene Carboamination," J. Org. Chem. 73, 6045-6047.

2007

P. H. Fuller, 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, S. R. Chemler (2007), "Copper(II)-Catalyzed Enantioselective Intramolecular Carboamination of Alkenes," J. Am. Chem. Soc. 129, 12948.

T. P. Zabawa, S. R. Chemler (2007). "Copper(II) Carboxylate Promoted Intramolecular Diamination of Terminal Alkenes: Improved Reaction Conditions and Expanded Substrate Scope," Org. Lett. 9, 2035-2038.

E. S. Sherman, P. H. Fuller, D. Kasi, S. R. Chemler (2007). "Pyrrolidine and Piperidine Formation Via Copper(II) Carboxylate Promoted Intramolecular Carboamination of Unactivated Olefins: Diastereoselectivity and Mechanism," J. Org. Chem. 72, 3896-3905.

S. R. Chemler, P. H. Fuller (2007). "Heterocycle Synthesis by Copper Faciliated Addition of Heteroatoms to Alkenes, Alkynes and Arenes," Chem. Soc. Rev.  36, 1153-1160 (invited review).

2005

T. P. Zabawa, D. Kasi and S. R. Chemler (2005). "Copper(II) Acetate Promoted Intramolecular Diamination of Unactivated Olefins," J. Am. Chem. Soc., 32, 11250-11251.

2004

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.

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. 6, 1573.

Vitamin E Collaboration

Y. Wu, K. Zu, J. Ni, S. Yeh, D. Kasi, N. S. James, S. R. Chemler, C. Ip (2004), "alpha-VItamin E Derivative, RRR-alpha-Tocopheryloxybutyrate: Lessons for the Design of Vitamin E Analog for Cancer Prevention," Anticancer Research, 24, 3795.

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.

J. Ni, T. Ma, M. A. DiMaggio, S. Xie, M. Chen, N. S. James, D. Kasi, I. Haque, S. R. Chemler, S. Yeh (2009), "Novel Vitamin E Analogs Inhibit Prostate Cancer Cell Growth in Vitro and In Vivo." Clin. Cancer Res. 15, 898-906.

Postdoc and Graduate Pubs

S. R. Chemler, U. Iserloh and S. J. Danishefsky (2001). "Toward an Enantioselective Synthesis of Phomactin A: Construction of the Oxadecalin Core via a Highly Stereoselective Diels-Alder Reaction," Org. Lett. 3, 2949-2951.
[Full text PDF]

S. R. Chemler and S. J. Danishefsky (2000). "Transannulaar Macrocyclization via Intramolecular B-Alkyl Suzuki Reaction," Org. Lett. 2, 2695-2698.
[Full text PDF]

S. R. Chemler, W. R. Roush (2003) "Stereochemistry of the Allylation and Crotylation Reactions of a-Methyl-b-Hydroxy Aldehydes with Allyl- and Crotyltrifluorosilanes. Synthesis of Anti, Anti-Dipropionate Stereotriads and Stereodivergent Pathways for the Reactions with 2,3-Anti and 2,3-Syn a-Methyl-b-Hydroxy Aldehydes," J. Org. Chem., 68, 1319-1333.
[Full text PDF] -- Fix this

S. R. Chemler and W. R. Roush (1999). "Stereochemically Divergent Pathways for the Allylation and Crotylation Reactions of Anti- and Syn-b-Hydroxy-a-Methyl Aldehydes with Allyl- and Crotyltrifluorosilanes," Tetrahedron Lett. 40, 4643-4647.
[Full text PDF]

S. R. Chemler, D. S. Coffey and W. R. Roush (1999). "An Improved Synthesis of the (E,Z)-Dienoate Precursor of (+)-Damavaricin D Via a Vinylogous Horner-Wadsworth-Emmons Reaction," Tetrahedron Lett. 40, 1269-1272.
[Full text PDF]

K. A. Scheidt, H. Chen, B. C. Follows, S. R. Chemler, D. S. Coffey and W. R. Roush (1998). "Tris(dimethylamino)sulfonium Difluorotrifmethylsilicate, a Mild Reagent for the Removal of Silicon Protecting Groups," J. Org. Chem. 63, 6436-6437.
[Full text PDF]

S. R. Chemler and W. R. Roush (1998). "Concerning the Synthesis of the Elusive anti,anti-Dipropionate Stereotriad via the Crotylation of a-Methyl-b-Hydroxy Aldehydes with (Z)-Crotyltrifluorosilane. Application to the Synthesis of the C(7)-C(16) Segment of Zincophorin," J. Org. Chem. 63, 3800-3801.
[Full text PDF]

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. Chemie. Int. Ed., 40, 4544-4568.
[Full text PDF]

 

Book Chapters (All)

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.

S. R. Chemler and T. P. Zabawa, Science of Synthesis (2006),Vol. 20a, 20.2.8. "Product Subclass 8: 2-Heteroatom-Substituted Alkanoic Acids" J. S. Panek, E. Jacobsen, Eds.

S. R. Chemler and T. P. Zabawa, Science of Synthesis (2006), Vol. 20b, 20.5.11. "Product Subclass 11: 2-Heteroatom-Substituted Alkanoic Esters" J. S. Panek, E. Jacobsen, Eds.

S. R. Chemler (2007/2008), "Isopropenyllithium, Second Update," in Encyclopedia of Reagents for Organic Synthesis," L. Paquette, editor,

S. R. Chemler, Science of Synthesis (2008), Vol. 40, 40.9. "Product Class Amido Derivatives of Sulfanediol," E. Schaumann, D. Enders, Eds.

S. R. Chemler, Science of Synthesis (2008), Vol. 40, 40.10. "Product Class Amido Derivatives of Sulfurous Acid," E. Schaumann, D. Enders, Eds.

E. S. Sherman, S. R. Chemler, Science of Synthesis (2008), Vol. 40, 40.11, "Product Class N-Alkylsulfamic Acids and Derivatives," E. Schaumann, D. Enders, Eds.

S. R. Chemler, "Roush Allylboronation" in Comprehensive Name Reactions, J. Li and E. J. Corey, Eds., 2010.

S. R. Chemler, "Stereoselective Nitrogen Heterocycle Synthesis Mediated by Chiral Metal Catalysts," Chap. 16 in Catalytic Methods in Asymmetric Synthesis: Advanced Materials, Techniques, and Applications, Wiley-VCH, M. Gruttadauria, Ed. 2011.

 

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