Blakemore, Paul R.

Education:
B.Sc., Chemistry, University of Southampton, Southampton, UK (1995); Ph.D.,

Chemistry, University of Glasgow, Glasgow, UK (1999).

Awards: Royal Society University Research Fellowship (2001-2004)

Research Group Website:
http://www.chemistry.oregonstate.edu/blakemore/

Organic & Bioorganic web site:
http://www.chemistry.oregonstate.edu/organic/

Research Interests

Research within the Blakemore Research Group is focused on the development of new methods and concepts for stereoselective synthesis.  Emphasis is placed on the following three areas: (a) study of novel axially chiral ambifunctional molecules with applications in catalysis, (b) development of the stereospecific reagent controlled homologation (StReCH) process as a unified reductionist synthetic paradigm, and (c) practical total synthesis of important alkaloid targets (e.g., sparteine, thebaine).

Representative Publications

"Spontaneous Symmetry Breaking During Interrupted Crystallization of an Axially Chiral Amino Acid Derivative," Sephton, M. A.; Emerson, C. R.; Zakharov, L. N.; Blakemore,* P. R. Chem. Commun. 2010, 46, 2094-2096. [LINK][abstract]  

"Thieme Chemistry Journal Awardees - Where Are They Now? Stereoselective Synthesis of Z-Configured alpha,beta-Unsaturated Macrocyclic Lactones and Diolides by Intramolecular Julia-Kocienski Olefination," Giesbrecht, H. E.; Knight, B. J.; Tanguileg, N. R.; Emerson, C. R.; Blakemore,* P. R. Synlett 2010, 374-378. [LINK][abstract] 1 citation  

"Total Synthesis of (±)-alpha-Isosparteine, (±)-beta-Isosparteine, and (±)-Sparteine From a Common Tetraoxobispidine Intermediate," Norcross, N. R.; Melbardis, J. P.; Ferris Solera, M.; Sephton, M. A.; Kilner, C.; Zakharov, L. N.; Astles, P. C.; Warriner, S. L.; Blakemore,* P. R. J. Org. Chem. 2008, 73, 7939-7951. [LINK][abstract] 4 citations  

"Determination of pKa Values for Diether Derivatives of 7,7´-Dihydroxy-8,8´-biquinolyl: Dependence of Basicity on Interannular Dihedral Angle," Blakemore,* P. R.; Milicevic, S. D.; Perera, H.; Shvarev, A.; Zakharov, L. N. Synthesis 2008, 2271-2277. [LINK][abstract]  

"Enzymatic Resolution of 7,7´-Dihydroxy-8,8´-biquinolyl Dipentanoate and Its Conversion to 2,2´-Di-tert-butyl-7,7´-dihydroxy-8,8´-biquinolyl," Blakemore,* P. R.; Milicevic, S. D.; Zakharov, L. N. J. Org. Chem. 2007, 72, 9368-9371. [LINK][abstract] 4 citations  

"Competing Reaction Pathways from alpha-Halo-alpha-protioalkyl Aryl Sulfoxides Initiated by Organometallic Reagents," Blakemore,* P. R.; Burge, M. S; Sephton, M. A. Tetrahedron Lett. 2007, 48, 3999-4002. [LINK] 1 citation  

"Iterative Stereospecific Reagent Controlled Homologation of Pinacol Boronates by Enantioenriched alpha-Chloroalkyllithium Reagents," Blakemore,* P. R.; Burge, M. S. J. Am. Chem. Soc. 2007, 129, 3068-3069. [LINK][abstract] 14 citations  

"A Stereocontrolled Synthesis of beta-Isosparteine," Blakemore,* P. R.; Norcross, N. R.; Warriner, S. L.; Astles, P. C. Heterocycles 2006, 70, 609-617. [LINK][abstract] 5 citations  

"Resolution, Enantiomerization Kinetics, and Chiroptical Properties of 7,7´-Dihydroxy-8,8´-biquinolyl," Blakemore,* P. R.; Kilner, C.; Milicevic, S. D. J. Org. Chem. 2006, 71, 8212-8218. [LINK][abstract] 5 citations  

"Reagent Controlled Asymmetric Homologation of Boronic Esters by Enantioenriched Main-Group Chiral Carbenoids," Blakemore,* P. R.; Marsden, S. P.; Vater, H. D. Org. Lett. 2006, 8, 773-776. [LINK][abstract] 16 citations  

"A Practical Synthesis of (±)-alpha-Isosparteine from a Tetraoxobispidine Core," Blakemore,* P. R.; Kilner, C.; Norcross, N. R.; Astles, P. C. Org. Lett. 2005, 7, 4721-4724. [LINK][abstract] 8 citations  

"Ethyl (Benzothiazol-2-ylsulfonyl)acetate: A New Reagent for the Stereoselective Synthesis of alpha,beta-Unsaturated Esters from Aldehydes," Blakemore,* P. R.; Ho, D. K. H.; Nap, W. M. Org. Biomol. Chem. 2005, 3, 1365-1368. [LINK][abstract] 23 citations  

"Harnessing Anionic Rearrangments on the Benzenoid Ring of Quinoline for the Synthesis of 6,6´-Disubstituted 7,7´-Dihydroxy-8,8´-biquinolyls," Blakemore,* P. R.; Kilner, C.; Milicevic, S. D. J. Org. Chem. 2005, 70, 373-376. [LINK][abstract] 8 citations