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Karl Dieter

Dr. Karl DieterProfessor
Organic Chemistry
Department Chair

Phone: (864) 656-2319
Office: 219A Hunter Laboratories
E-mail: dieterr@clemson.edu

Research Interests | Publications | Study Guide

Dr. Dieter, professor, received his B.A. (1973) from Lehigh University and his Ph.D. (1978) from the University of Pennsylvania working in synthesis, synthetic methods, and photochemistry with Prof. Amos B. Smith III. He was an American Chemical Society Postdoctoral Fellow (1978-1979) with Prof. Jerrold Meinwald at Cornell in natural products chemistry. He served on the faculty at Boston University before joining Clemson in 1985.

Research Interests

Dr. Dieter's research in new synthetic methods involves organocopper, organopalladium and organosulfur chemistry and focuses on asymmetric synthesis. The general availability of enantioselective procedures remains one of the major problems in organic chemistry and is particularly important to the pharmaceutical industry.

example oneDr. Dieter's development of a-aminoalkylcuprates, supported by the National Institutes of Health and the National Science Foundation, provides a facile method for functionalization adjacent to an amine or amide nitrogen atom. Reactions of N-Boc (tert-butoxy carbonyl) carbamate derived cuprates with a,ß-unsaturated carboxylic acid derivatives, vinyl triflates, vinyl iodides, acid chlorides, and allylic and propargylic substrates have been reported.

Efforts are under way to use these reactions in alkaloid natural product synthesis (e.g., indolizidine alkaloid 167B, a blocker of nerve ransmissions). The enantio selective vinylation of chiral a- aminoalkylcuprates holds considerable promise for the asymmetric synthesis of a wide range of naturally occurring alkaloids. Utilization of a-aminoalkylcuprates also provides synthetic routes to kainic acids, aza sugars, preussin and aspidospermidine alkaloids. Attention is focused on developing synthetic routes to pyrrolizidine and indolizidine alkaloids and aza sugars which display a wide range of biological activity (e.g., inhibitory effects on viruses, retroviruses, tumor cells and enzymatic pathways).

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Publications

Dieter RK, Huang YX, & Guo FH (2012) Regio- and Stereoselectivity in the Reactions of Organometallic Reagents with an Electron-Deficient and an Electron-Rich Vinyloxirane: Applications for Sequential Bis-Allylic Substitution Reactions in the Generation of Vicinal Stereogenic Centers. Journal of Organic Chemistry 77(11):4949-4967.

Dieter, R. K.; Guo, F. H., Conjugate Addition Reactions of N-Carbamoyl-4-Pyridones with Organometallic Reagents. Journal of Organic Chemistry 2009, 74 (10), 3843-3848.

Dieter, R. K.; Guo, F. H., Tandem regio- and stereoselective organocuprate-mediated bis-allylic substitutions. Organic Letters 2008, 10 (10), 2087-2090.

Dieter, R.K., C.M. Topping, and L.E. Nice, A study of factors affecting alpha-(N-carbamoyl)alkylcuprate chemistry. J. Org. Chem., 2001. 66(7): p. 2302-2311.

Dieter, R.K., C.M. Topping, K.R. Chandupatla, and K. Lu, Enantioselectivity in the reactions of chiral alpha-(N- carbamoyl)alkylcuprates. J. Am. Chem. Soc., 2001. 123(21): p. 5132-5133.

Dieter, R.K. and H. Yu, Synthesis of 3-pyrrolines, annulated 3-pyrrolines, and pyrroles from alpha-Amino allenes. Org. Lett., 2001. 3(24): p. 3855-3858.

Dieter, R.K., C.W. Alexander, and L.E. Nice, Conjugate addition reactions of alpha-aminoalkylcuprates with alpha,beta-enones and enals. Tetrahedron, 2000. 56(18): p. 2767-2778.

Dieter, R.K. and H.Y. Yu, A facile synthesis of polysubstituted pyrroles. Org. Lett., 2000. 2(15): p. 2283-2286.

Dieter, R.K., K. Lu, and S.E. Velu, Conjugate addition reactions of alpha-aminoalkylcuprates with alpha,ß-alkenyl-, alpha,ß-alkynyl-, alpha,ß- ß,gamma-allenyl-, and alpha,ß-gamma,delta-dienyl carboxylie acid derivatives, nitriles, and sulfoxides. J. Org. Chem., 2000. 65(25): p. 8715-8724.

Dieter, R.K., Reaction of acyl chlorides with organometallic reagents: A banquet table of metals for ketone synthesis. Tetrahedron Lett., 1999. 55(14): p. 4177-4236.

Dieter, R.K. and K. Lu, Stereoselective synthesis of 4-alkylidene pyrrolidinones and pyrrolizidinones. Tetrahedron Lett., 1999. 40(21): p. 4011-4014.

Dieter, R.K. and L.E. Nice, Synthesis of amino allenes via reaction of alpha- aminoalkylcuprates with propargyl substrates. Tetrahedron Lett., 1999. 40(23): p. 4293-4296.

R. K. Dieter, "Reaction of Acyl Chlorides with Organometallic Reagents: A Banquet Table of Metals for Ketone Synthesis", Tetrahedron, 55, 4177-4336 (1999).

R. K. Dieter, C. W. Alexander, L. E. Nice, "Conjugate Addition Reactions of a-Amino- alkylcuprates with a,b-Enones and Enals", Tetrahedron, 56, 2767-2778 (2000).

R. K. Dieter, H. Yu , "A Facile Synthesis of Polysubstituted Pyrroles", Org. Lett., 2, 2283-2286 (2000).

R. K. Dieter, K. Lu, S. E. Velu, "Conjugate Addition Reactions of a-Aminoalkylcuprates with a,ß-Alkenyl-, a,ß-Alkynyl-, a,ß-ß,gAllenyl-, and a,ß-g,d-Dienyl Carboxylic Acid Derivatives, Nitriles, and Sulfoxides", J. Org. Chem., 65, 8715-8724 (2000) .

R. K. Dieter, C. M. Topping and L. E. Nice, "A Study of Factors Affecting a-Aminoalkylcuprate Chemistry", J. Org. Chem., 66, 2302 (2001).

Dieter, R. K.; Topping, C. M.; Chandupatla, K. R.; Lu, K. "Enantioselectivity in the Reactions of Chiral a-(N-carbamoyl)alkylcuprates", J. Am. Chem. Soc., 123, 5132-5133, (2001).

Dieter, R. K.; Yu, H. "Synthesis of 3-Pyrrolines, Annulated 3-Pyrrolines, and Pyrroles from a-Amino Allenes", Org. Lett., 3, 3855-3858, (2001).

Dieter, R. K.; Lu, K. "a-(N-Carbamoyl)alkylcuprate Chemistry in the Synthesis of Nitrogen Heterocycles", J. Org. Chem., 67, 847-855, (2002).

R. K. Dieter "Heteroatom and a-Heteroatomalkylcuprates in Organic Synthesis", In Modern Organocopper Chemistry, Ed. Krauss: Wiley-VCH, Weinheim, 2002, p. 79.

Dieter, R. K.; Sharma, R. R.; Yu, H.; Gore, V. K. "Acylation of a-(N-Carbamoyl)alkylcuprates and of Alkyl- and Aryl(halo)cuprates", Tetrahedron, In Press.

Li, S.; Dieter, R. K. "Coupling Reactions of a-(N-Carbanoyl)alkylcuprates with Enol Triflates Derived from Cyclic-b-Keto Esters: A Facile Approach to g-Carbamoyl-a,b-Enoates", J. Org. Chem., In Press.

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Study Guide

"Of Symbols, Electrons and Xanadu: The Language of Organic Chemistry"
by Dr. R. Karl Dieter

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