Neil E. Schore

Professor

Email: schore@chem.ucdavis.edu

Organic Chemistry

B.A., University of Pennsylvania, 1969. NSF and NIH Predoctoral fellowships, 1969-73. Louis P. Hammett Award, 1973. Ph.D., Columbia University, 1973. NIH Postdoctoral Fellowship, 1974-76. Appointed to faculty, UC Davis, 1976-. Magnar Ronning Award, Teaching Excellence, 1979. Dreyfus Teacher-Scholar, 1981-85. Distinguished Teaching Award, 1989. Executive Secretary, UC Cancer Research Coordinating Committee, 1999-. Phi Beta Kappa Award for Teaching Excellence, 2006.

Research Interests

Design of transition metal reagents for organic synthesis; development of organic synthesis methodology using insoluble polymer supports.

Our major area of current research involves the use of polymer attachment of organic substrates to modify or completely change their reactivity. Our initial efforts in this area revealed that we could induce major changes in reaction selectivity in both conventional synthetic processes and transition-metal catalyzed reactions. For example, in organic cycloaddition reactions, we can selectively cyclize just one of the double bonds of a symmetrical diene to a polymer-supported 1,3-dipole precursor, leaving the other one free for use at a later stage of a synthesis of substituted cyclic ethers. In another instance, organometallic reaction between an alkene and an alkyne can be selectively promoted, and reactions between multiple alkyne units suppressed by use of polymer-attachment strategies. We are pursuing a variety of avenues of research in this area, such as study of the use of entirely novel polymer types for the recycling and reuse of organic and organometallic reagents and catalysts.

Publications

• Varela, M. C., S. M. Dixon, M. D. Price, J. E. Merit, P. E. Berget, S, Shiraki, M. J. Kurth and N. E. Schore. 2007. Comparison of enantioselective reductions using bead and monolith ‘disk’ polymer formulations of CBS catalysts. Tetrahedron, 63, in press.
• Hok, S. and N. E. Schore. 2006. Synthesis of 2-arylcycloalka-2,4-dienones using sulfone-based methodology. J. Org. Chem., 71, 1736.
• Berget, P. E. and N. E. Schore. 2006. Recycling titanocene dichloride from the Petasis methylenation reaction. Organometallics, 25, 552.
• Berget, P. E. and N. E. Schore. 2005. Catalytically active, recyclable polymeric. Titanocene disks: a batch-flow reactor. Tet. Lett., 46, 8869.
• Song, Y., R. E. Haddad, S.-L. Jia, S. Hok, M. M. Olmstead, D. J. Nurco, N. E. Schore, J. Zhang, J.-G. Ma, K. M. Smith, S. Gazeau, J. Pécaut, J.-C. Marchon, C. J. Medforth and J. A. Shelnett. 2005. Energetics and structural consequences of axial ligand coordination in nonplanar nickel porphyrins. J. Am. Chem. Soc., 127, 1179.
• Ockey, D.A., M.A. Lewis and N.E. Schore. 2003. A short synthesis of (±)-tecomanine via a Pauson-Khand-based route. Tetrahedron, 58, 5377.
• Price, M.D., J.K. Sui, M.J. Kurth and N.E. Schore. 2002. Oxazaborolidenes as functional monomers: ketone reduction using polymer-supported CBS catalysts. J. Org. Chem., 67, 8086.
• Price, M.D., M.J. Kurth and N.E. Schore. 2002. Comparison of solid phase and solution phase chiral auxiliaries in the alkylation/iodolactonization sequence to ?-butyrolactones. J. Org. Chem., 67, 7769.
• Hok, S., J. Vassilian and N.E. Schore. 2002. Catalytically active, recyclable zirconocene supported at crosslinks within porous polymer disks. Org. Lett., 4, 2365.
• Cutter, P.S., R.B. Miller and N.E. Schore. 2002. Synthesis of Protoberberines using a silyl-directed Pictet-Spengler cyclization. Tetrahedron, 58, 1471.
• Montierth, J.M., A.G. Duran, S.H. Leung, K.M. Smith and N.E. Schore. 2000. The polymer-supported MacDonald-type porphyrin synthesis: Coupling of two dissimilar dipyrromethanes. Tet. Lett., 41, 7423.
• Breczinski, P.M., A. Stumpf, H. Hope, M. E. Krafft, J.A. Casalnuovo and N.E. Schore. 1999. Stereoselectivity in the intramolecular Pauson-Khand reaction: Towards a simple predictive model. Tetrahedron, 55, 6797.
• Montierth, J.M., D.R. DeMario, M.J. Kurth and N.E. Schore. 1998. The polymer-supported Cadiot-Chodkiewicz coupling of acetylenes to produce unsymmetrical diynes. Tetrahedron, 54, 11741.
• Spitzer, J.L., M.J. Kurth, N.E. Schore and S.D. Najdi. 1997. Polymer-supported synthesis as a tool for improving chemoselectivity: Pauson-Khand Reaction. Tetrahedron, 53, 6791.
• Beebe, X., C.L. Chiappari, M.M. Olmstead, M.J. Kurth and N.E. Schore. 1995. Polymer-supported synthesis of cyclic ethers: Electrophilic cyclization of tetrahydrofuroisoxazolines. J. Org. Chem., 60, 4204.
• Beebe, X., N.E. Schore and M. J. Kurth. 1995. Polymer-supported synthesis of cyclic ethers: Electrophilic cyclization of isoxazolines. J. Org. Chem., 60, 4196.
• Moon, H., N.E. Schore and M.J. Kurth. 1994. A polymer-supported C2-symmetric chiral auxiliary: Preparation of non-racemic 3,5-disubstituted ?-butyrolactones. Tet. Lett., 35, 8915.
• Casalnuovo, J.A., R.W. Scott, E.A. Harwood, and N.E. Schore. 1994. First example of reversal of normal stereoselectivity in the intramolecular Pauson-Khand reaction. Tet. Lett., 35, 1153.
• Beebe, X., C.L. Chiappari, M.J. Kurth, and N.E. Schore. 1993. An intramolecular 1,3-dipolar cycloaddition/electrophilic cyclization sequence to give cyclic ethers. J. Org. Chem., 58, 7320.
• Rowley, E.G. and N.E. Schore. 1992. The Pauson-Khand reaction in triquinane synthesis: Approaches to pentalenene, pentalenenic acid, and silphinene. J. Org. Chem., 57, 6853.
• Beebe, X., N.E. Schore and M.J. Kurth. 1992. Polymer-supported synthesis of 2,5-disubstituted tetrahydrofurans. J. Amer. Chem. Soc., 114, 10061.