Office: Room 607, 17 Lex., Phone: (646) 660-6243, E-mail: Keith_Ramig@baruch.cuny.edu

Keith M. Ramig, Ph. D., University of Pittsburgh (Organic Chemistry), has many publications dealing with organic synthesis, most recently in the area of organofluorine chemistry. While working at various local pharmaceutical companies as a process R & D chemist, he was responsible for finding new synthetic routes to several drug candidates. His current research involves stereoselective synthesis of fluorine-atom-containing molecules which are used as anesthetics. Another area of his research deals with the discovery of improved reagents for introduction of fluorine atoms into molecules. Since coming to Baruch in 1998, he has involved undergraduate students in his research, which is funded primarily by the National Science Foundation. His students have been co-authors of many conference presentations and journal articles.

 

RESEARCH
"It has become clear that many single-enantiomer drugs have vastly improved pharamcological properties over the racemic mixture. My research is aimed at synthesizing single enantiomers of inhaled anesthetics, most of which are chiral fluorinated compounds. To do this, I and my collaborators have made a reaction known as anionic decarboxylation behave stereoselectively, which has only been successful for a few cases in the past."

Publications 1995-present

K. Ramig, S. Alli, M. Cheng, R. Leung, R. Razi, M. Washington, L. V. Kudzma
      “Synthesis of 2,4-Diaryl-3H-1-benzazepines” Synlett, 2868-2870, 2007.
K. Ramig
      “(+/-)-Halothane (2-bromo-2-chloro-1,1,1-trifluoroethane)” Electronic Encyclopedia of Reagents for Organic Synthesis, 2007. www.mrw.interscience.wiley.com/eros/articles/rn00729/frame.html
K. Ramig
      "Synthesis and Reactions of Fluoroether Anesthetics." Synthesis, 2002, 2627-2631.
R. L. Hanson, P. A. Jass, W.-S. Li, R. Patel, K. Ramig, J. J. Venit
      R. L. Hanson, P. A. Jass, W.-S. Li, R. Patel, K. Ramig, J. J. Venit, "Substituted Alkylketo Compounds and Process." US Patent 6486331, 2002 (Bristol-Myers Squibb Co.).
R. Hanson, M. J. Donovan, S. Goldberg, P. A. Jass, W.-S. Li, R. Patel, K. Ramig, L. J. Szarka, J. J. Venit
      R. Hanson, M. J. Donovan, S. Goldberg, P. A. Jass, W.-S. Li, R. Patel, K. Ramig, L. J. Szarka, J. J. Venit, "Stereoselective Reductive Amination of Ketones." US Patent 6468781, 2001 (Bristol-Myers Squibb Co.).
K. Ramig, M. Englander, F. Kallashi, L. Livchits, J. Zhou
      "Synthesis of Esters by Selective Methanolysis of the Trifluoromethyl Group." Tetrahedron Letters, 2002, 43:7731-7734.
J. D. Godfrey, Jr., D. R. Kronenthal, M. D. Schwinden, S. K. Srivastava, K. Ramig, J. J. Venit, P. A. Jass, S. Racha, J. L. Dillon, Jr., N. Soundararajan, G. L. Powers, A. S. Kotnis
      "Preparation of (S)-2-Amino-6,6-dimethoxyhexanoic Acid Methyl Ester via Novel Dioxolanes." US Patent 6248882, 2001 (Bristol-Myers Squibb Co.).
L. V. Kudzma, C. G. Huang, R. A. Lessor, L. A. Rozov, S. Afrin, F. Kallashi, C. McCutcheon, K. Ramig*
      "Diisopropylethylamine Mono(hydrogen fluoride) for Nucleophilic Fluorination of Sensitive Substrates: Synthesis of Sevoflurane." Journal of Fluorine Chemistry, 2001, 111, 11.
K. Ramig
      "Chiral Fluorinated Anesthetics." In Asymmetric Organofluorine Chemistry, P. V. Ramachandran, Ed.; American Chemical Society, 2000.
J. Moniot, S. K. Srivastava, W. J. Winter, J. J. Venit, S. Swaminathan, K. Ramig, P. A. Jass, M. D. Schwinden, J. L. Dillon, Jr., S. Racha, J. Simpson, C.-K. Chen, S. K. Pack
      "Preparation of [4S-(4.alpha.,7.alpha.,10a_)]-4-amino-octahydro-5-oxo-7H-pyrido[2,1 -b] [1,3]thiazepine-7-carboxylic Acid, Methyl Ester and Salts thereof via Novel Disulfides," US Patent 6162913, 2000 (Bristol-Myers Squibb Co.).
R. Hanson, M. J. Donovan, S. Goldberg, P. A. Jass, W.-S. Li, R. Patel, K. Ramig, L. J. Szarka, J. J. Venit
      "Stereoselective Reduction of Ketones," US Patent 6140088, 2000 (Bristol-Myers Squibb Co.).
K. Ramig,* L. V. Kudzma, R. A. Lessor, L. A. Rozov
      "Acid Fluorides and 1,1-Difluoroethyl Methyl Ethers as Fluoride Sources in Halogen-Exchange Reactions." J. Fluorine Chem. 1999, 94, 1.
P. L. Polavarapu,* C. Zhao, K. Ramig
      "Vibrational Circular Dichroism, Absolute Configuration and Predominant Conformations of Volatile Anesthetics: 1,2,2,2-Tetrafluoroethyl Methyl Ether." Tetrahedron: Asymmetry 1999, 10, 1099.
Keith Ramig,* Donald Halpern
      "Asymmetric Syntheses and Resolutions of Fluorinated Volatile Anesthetics" In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets, V. Soloshonok, Ed.; John Wiley & Sons: Chichester, 1999.
L. V. Kudzma, R. A. Lessor, L. A. Rozov, K. Ramig
      "Method of Preparing Monofluoromethyl Ethers." US Patent 5886239, 1999 (Baxter International).
L. A. Rozov, R. A. Lessor, L. V. Kudzma, K. Ramig*
      "The Fluoromethyl Ether Sevoflurane as a Fluoride Source in Halogen-Exchange Reactions." J. Fluorine Chem. 1998, 88, 51.
L. A. Rozov, C. G. Huang, D. F. Halpern, G. G. Vernice, K. Ramig*
      "Enantioselective Synthesis of the Volatile Anesthetic Desflurane." Tetrahedron: Asymmetry 1997, 8, 3023.
R. A. Lessor, L. V. Kudzma, K. Ramig
      "Methods for Preparing 5-Aroyl-1,2-dihydro-3H-pyrrolo-[1,2a]pyrrole-1-carboxylic acids." US Patent 5621115, 1997 (Ohmeda).
K. Ramig,* F. Quiroz, G. G. Vernice, L. A. Rozov
      "Selective Free-Radical Dechlorination of 1,1-Dichloro-2,2,2-trifluoroethyl Difluoromethyl Ether Initiated Thermally or by UV Light: A Practical and 'Green' Method for Isoflurane Synthesis." J. Fluorine Chem. 1996, 80, 101.
K. Ramig, Y. Dong, S. D. Van Arnum*
      "A Convenient Preparation of Cyclobutyl Ketones: The Lithium Naphthalenide-Catalyzed Cyclization of Substituted 1,4-Dihalobutanes." Tetrahedron Letters 1996, 443.
S. D. Van Arnum,* K. Ramig, N. Stepsus, Y. Dong
      "An Improved Procedure for the Preparation of Styryl Thiazoles." Tetrahedron Letters 1996, 8659.
K. Ramig,* A. Krishnaswami, L. A. Rozov
      "Enantiomeric Resolution of the Fluoroether Anesthetics Isoflurane, Desflurane, Enflurane, and Analogues by Capillary Gas Chromatography and Nuclear Magnetic Resonance Spectroscopy using Modified Cyclodextrins: A Simple Method for Column-Suitability Screening." Tetrahedron 1996, 52, 319.
L. A. Rozov, K. Ramig*
      "New Synthesis of (+)-(S)-Halothane." Chirality 1996, 8, 3.
K. Ramig, J. J. Landi, Jr.
      "Process for the Preparation of (R)-3-Hexyl-5,6-dihydro-4-hydroxy-6-undecyl-2H-pyran-2-one and (R)-5,6-dihydro-6-undecyl-2H-pyran-2,4(3H)-dione." US Patent 5420305, 1995 (Hoffmann-La Roche).
K. Ramig,* L. Brockunier, P. W. Rafalko, L. A. Rozov
      "Carbon-Carbon Bond Cleavage which Results in Inversion of Configuration: Conversion of (R)-(+)-1-Methoxytetrafluoropropionic Acid to (S)-(-)-1,2,2,2-Tetrafluoroethyl Methyl Ether." Angew. Chem., Int. Ed. Engl. 1995, 34, 222.
L. A. Rozov, P. W. Rafalko, S. M. Evans, L. Brockunier, K. Ramig*
      "Asymmetric Synthesis of the Volatile Anesthetic 1,2,2,2-Tetrafluoroethyl Chlorofluoromethyl Ether Using a Stereospecific Decarboxylation of Unusual Stereochemical Outcome." J. Org. Chem. 1995, 60, 1319.