Organic chemistry; creation, resolution, and use of very pure chiral building blocks for asymmetric synthesis
- B.A., 1953, Oberlin College
- Ph.D., 1960, Ohio State University
- Postdoctoral Fellow, 1963-1965, University of Wisconsin
Honors & Awards:
National Institute of Health Postdoctoral Fellowship, 1963-1965
A cheap, scalable synthesis of racemic 3-halo-2-methyl-1-propanol (halo = Cl, Br, I) has been developed. Resolution into pure enantiomers will afford new alternatives to existing C4 chiral building blocks, and new routes to C5 chiral building blocks. These can open significantly shortened routes to (e.g.) pharmaceuticals, agrochemicals, pheromones, and perfumes. Also under study are new chiral auxiliaries that can improve separations by crystallization and chromatography, catalyze stereoselective reactions, and enable convenient nmr assay of stereomeric purity.
- Mekala, S.; Hahn, R. A Scalable, Nonenzymatic Synthesis of Highly Stereopure Difunctional C4 Secondary Methyl Linchpin Synthons, J. Org. Chem. 2015, 80, 1610-1617.
- Mekala, S.; Hahn, R. Process intensification-assisted conversion of alpha, omega-alkanediols to dibromides. Tetrahedron Letters, 2015, 56, 630-632.
- Gries, R.; Schaefer, P. W.; Hahn, R.; Khaskin, G.; Ramaseshiah, G.; Singh, B.; Hehar, G. K.; Gries, G. J. Sex Pheromone Components of Indian Gypsy Moth, Lymantria Obfuscata. Chem. Ecol. 2007, 33, 1774-1786.
- Alexander, J. S.; Zuniga, M.; Guino-o, T.; Hahn, R.; Ruhlandt-Senge, K. The Organometallic Chemistry of the Alkaline Earth Metals. Chapter in The Encyclopedia of Inorganic Chemistry, Wiley, 2005.
- Gries, R.; Khaskin, G.; Schaefer, P. W.; Hahn, R.; Gotoh, T.; Gries, G. J. (7R,8S)-cis-7,8-Epoxy-2-methyloctadec-17-ene: A Novel Trace Component from the Sex Pheromone Gland of Gypsy Moth, Lymantria dispar. Chem. Ecol. 2005, 31, 49-62.
- Khrimian, A.; Oliver, J. E.; Hahn, R. C.; Dees, N. H.; White, J.; Mastro, V. C. Improved Synthesis and Deployment of (2S,3R)-2-(2Z, 5Z-Octadienyl)-3-nonyloxirane, a Pheromone of the Pink Moth Lymantria Mathura. J. Agric. Food Chem. 2004, 52, 2890-2895.