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Faculty

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Robert K. Boeckman, Jr.

  • Marshall D. Gates, Jr. Professor of Chemistry

PhD, Brandeis University, 1971

451 Hutchison Hall
(585) 275-4229
rkb@rkbmac.chem.rochester.edu


Research Overview

Professor Boeckman's research efforts focus on the development of new synthetic methodology, applicable solution of complex stereochemical problems, including asymmetric synthesis. His research employs organometallic chemistry and conformational theory to assist creation of stereocontrolled synthetic transformations and utilizes complex multifunctional molecules as target structures for applications of his methodological studies.

Currently, Professor Boeckman's research group is developing new methodology for asymmetric synthesis using novel chiral auxiliaries, ligands, and associated metal complexes as catalysts based upon a family of chiral bicyclic lactams derived from camphor and pinene. Other goals include the creation of medium rings via the retro-Claisen rearrangement. These methodologies, among several, are being applied to the total synthesis of a variety of biologically significant natural products which requires the use of the full range of modern analytical instrumentation, including HPLC, high field NMR, GC-MS, and X-ray crystallography.

Figure 1.

Research by Dr. Boeckman and his group provides new tools and methodologies for preparative organic chemistry which have practical application in the areas of medicinal chemistry relevant to the pharmaceutical industry.

Selected Publications

  • Boeckman, R. K. Jr., Biegasiewicz, K.F., Pero, J.E., Tusch, D.J., Miller, J.R. "The Total Synthesis of (-)-Rasfonin," J. Org. Chem. 2014, 79, Submission Anticipated.
  • Boeckman, R. K. Jr., Biegasiewicz, K.F., Tusch, D.J., Miller, J.R. "The Asymmetric Hydroxymethylation of Aldehydes: Mechanistic Aspects and Optimization," J. Org. Chem. 2014, 79, Submitted.
  • Boeckman, R. K. Jr., Tusch, D.J., Biegasiewicz, K.F. "The Asymmetric Hydroxymethylation of Aldehydes," Organic Syntheses 2014, Submitted.
  • Boeckman, R. K. Jr. "Total Synthesis of a Possible Specific and Effective Acid-targeted Cancer Diagnostic, a Camphor Derived Bis-N-oxide Dimer," Tetrahedron Lett. 2011, 52, 2243-2245.
  • Cody, R.J., Boeckman, R. K. Jr. "Terpene Derived Auxiliaries: Camphor and Pinene Derived Auxiliaries," Synthetic Methods II - Chiral Auxiliaries, Comprehensive Chirality 2012, vol. 3 R. K. Boeckman, Jr., Ed.; Elsevier Science, Oxford UK, 1148-1211.
  • Boeckman, R. K., del R. Ferreira, M. R., Mitchell, L. H., Shao, P., Neeb, M. J., Fang, Y. "Studies Culminating in the Total Synthesis and Determination of the Absolute Configuration of (-)-Saudi," Tetrahedron Lett. 2011, 67, 9787-9808.
  • Boeckman, R. K., Miller, Y., Savage, D., Summerton, J. E. "Total Synthesis of a Possible Specific and Effective Acid-targeted Cancer Diagnostic, a Camphor Derived Bis-N-oxide Dimer," Tetrahedron Lett. 2011, 52, 2243-2245.
  • Boeckman, R. K., Miller, Y., Ryder, T. R. "Isoamidinium Salts: A New Class of Chiral and Achiral Dienophiles for Diels-Alder Reactions," Org. Lett. 2010, 12, 4524-4527.
  • Boeckman, R. K., Genung, N. E., Chen, K., Ryder, T. R. "Synthetic and Mechanistic Studies of the Aza-Retro-Claisen Rearrangement. A Facile Route to Medium Ring Nitrogen Heterocycles," Org. Lett. 2010, 12, 1628-1631.
  • Boeckman, R. K. Miller, J. R. "Direct Enantioselective Organocatalytic Hydroxymethylation of Aldehydes Catalyzed by α,α-Diphenylprolinol Trimethylsilyl Ether," Org. Lett. 2009, 11, 4544-4547.
  • Boeckman, R. K., Jr., Collison, C. G., E-Eros "1,7,7-Trimethyl-2-azabicyclo[2.2.1]-heptan-3-one," Encyclopedia of Reagents for Organic Synthesis 2008, John Wiley & Sons, Chichester, UK., DOI: 10.1002/047084289X.rn00901
  • Boeckman, R. K., Jr., Collison, G. C., E-Eros "1,7,7-Trimethyl-3-azabicyclo[2.2.1]-heptan-2-one," Encyclopedia of Reagents for Organic Synthesis 2008, John Wiley & Sons, Chichester, UK., DOI: 10.1002/047084289X.rn00900
  • Boeckman, R. K., Jr., Hanson, S. M., Cody, J. A. "Alkylation of 2-Butyl-4,4-dimethyl-4H-benzo[d][1,3]oxathiien-1,1-dioxide, a New Class of Acyl Anion Equivalents as an Alternative to Dithianes," Heterocycles 2006, 70, 519-530.
  • Boeckman, R. K., Jr., Shao, P., Wrobleski, S. T., Boehmler, D. J., Heintzelman, G. R., Barbosa, A. J. " "Toward the Development of a General Chiral Auxiliary. A Total Synthesis of (+)-Tetronolide via a Tandem Ketene-Trapping [4 + 2] Cycloaddition Strategy," J. Am. Chem. Soc. 2006, 128, 10572-10588.
  • Boeckman, R. K., Jr., Pero, J. E., Boehmler, D. J. "Toward the Development of a General Chiral Auxiliary. Enantioselective Alkylation and a New Catalytic Asymmetric Addition of Silyloxyfurans: Application to a Total Synthesis of (-)-Rasfonin," J. Am. Chem. Soc. 2006, 128, 11032-11033.
  • Boeckman, R. K., Jr., Reeder, L. M. "Toward the development of a general chiral auxiliary 10: Enhancement of diastereoselectivity in Diels-Alder reactions of imides derived from a new bicyclic lactam chiral controller molecule," Synlett 2004, 8, 1399-1403.
  • Boeckman, R. K., Jr., Ferreira, M. R. R., Mitchell, L. H., Shao, P. "An Enantioselective Total Synthesis of (+) and (-)-Saudin. Determination of the Absolute Configuration," J. Am. Chem. Soc. 2002, 124, 190-191.
  • Boeckman, R. K., Jr., Clark, T. J., Shook, B. J. "A Practical Enantioselective Total Synthesis of the Bengamides B, E, and Z," Org. Lett. 2002, 4, 2109-2112.
  • Boeckman, R. K., Jr., Liu, X. "Controllable Monoaddition of Carbon Nucleophiles to 1,2,3,4-diepoxybutane: Two-directional Chain Extension of a C2 Symmetric Four Carbon Diepoxide as a Route to Differentiated Syn-1,2-Diols," Synthesis 2002, 14, 2138-2142.
  • Boeckman, R. K., Jr., Zhang, J., Reeder, M. R. "Synthetic and Mechanistic Studies of the Retro-Claisen Rearragement 4. Application to an Enantioselective Total Synthesis of (+)-Laurenyne," Org. Lett. 2002, 4, 3891-3894.
  • Boeckman, R. K., Jr., Clark, T. J., Shook, B. J. "The Development of a Convergent Efficient Enantioselective Synthesis of the Bengamides Via a Common Polyol Intermediate," Helv. Chim. Acta 2002, 85, 4532-4560.