Martin J. O'Donnell
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Loren T. Jones Award, 1981; Purdue School of Science Research Award, 1983; NCU Fellowship, 1992; Chancellor's Award for Excellence in Teaching, 1995; President's Award for Distinguished Teaching, 1996.
Research
We are developing methods for the preparation of optically active unnatural α-amino acids by carbon-carbon bond-forming reactions. A catalytic enantioselective reaction of a commercially available glycine anion equivalent (Ph2C=NCH2CO2tBu) using a chiral, non-racemic catalyst (Q*X) derived from the cinchona alkaloids under phase-transfer or homogeneous conditions provides products 1 in high enantioselectivity (up to 97% ee). A complementary cationic equivalent, which involves reaction of an acetate [Ph2C= NCH(OAc)CO2tBu] with nucleophiles in the presence of a palladium catalyst with chiral BINAP ligands, gives products such as 2 in up to 80% ee.
Recently we have extended our chemistry to the resin-bound synthesis of unnatural amino acids and peptides, termed “UPS” (unnatural peptide synthesis). This methodology, which involves introduction of an unnatural amino acid side chain during a normal solid-phase peptide synthesis (3 to 4, where X is oxygen or a peptide residue), provides ready access to a variety of different amino acid and peptide products using combinatorial chemistry.
Recent Publications
W. L. Scott, J. G. Martynow, J. C. Huffman and M. J. O'Donnell "The solid-phase synthesis of multiple classes of peptidomimetics from versatile resin-bound aldehyde intermediates" Journal of the American Chemical Society 2007, 129, 7077-7088.
P. V. Ramachandran, S. Madhi and M. J. O'Donnell "Synthesis of fluorinated glutamic acid derivatives via vinylalumination" Journal of Fluorine Chemistry 2007, 128, 78-83.
M. J. O'Donnell, J. D. Keeton, V. V. Khau and J. C. Bollinger "The regioselective α-alkylation of the benzophenone imine of glycinamide, alaninamide, and related derivatives" Canadian Journal of Chemistry 2006, 84, 1301-1312.
P. V. Ramachandran, S. Madhi and M. J. O'Donnell "Regioselective hydroboration-oxidation and -amination of fluoro-substituted styrenes" Journal of Fluorine Chemistry 2006, 127, 1252-1255.
P. V. Ramachandran, S. Madhi, L. Bland-Berry, M. V. R. Reddy and M. J. O'Donnell "Catalytic enantioselective synthesis of glutamic acid derivatives via tandem conjugate addition-elimination of activated allylic acetates under chiral PTC conditions" Journal of the American Chemical Society 2005, 127, 13450-13451.
J. Alsina, W. L. Scott and M. J. O'Donnell "Solid-phase synthesis of α-substituted proline hydantoins and analogs" Tetrahedron Letters 2005, 46, 3131-3135.
M. J. O'Donnell "The enantioselective synthesis of α-amino acids by phase-transfer catalysis with achiral Schiff base esters" Accounts of Chemical Research 2004, 37, 506-517.
W. L. Scott, J. Alsina, J. H. Kennedy and M. J. O'Donnell "Solid- phase synthesis of constrained terminal and internal lactam peptidomimetics" Organic Letters 2004, 6, 1629-1632.
M. J. O'Donnell, J. Alsina and W. L. Scott "Solid-phase synthesis and utilization of side-chain reactive unnatural amino acids" Tetrahedron Letters 2003, 44, 8403-8406.
W. L. Scott, J. Alsina and M. J. O'Donnell "The manual and automated solid-phase synthesis of α-substituted prolines and homologues" Journal of Combinatorial Chemistry 2003, 5, 684-692.
M. J. O'Donnell, J. T. Cooper and M. M. Mader "Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of β-substituted α-amino acid derivatives" Journal of the American Chemical Society 2003, 125, 2370-2371.
M. J. O'Donnell, M. D. Drew, J. T. Cooper, F. Delgado and C. Zhou "The enantioselective synthesis of α-amino acid derivatives via organoboranes" Journal of the American Chemical Society 2002, 124, 9348-9349. (for a press release entitled: "Enantioselective borane route to amino acids" see: Chemical & Engineering News, August 10, 2002, p 30).
W. L. Scott, M. J. O'Donnell, F. Delgado and J. Alsina "A solid-phase synthetic route to unnatural amino acids with diverse side chain substitutions" J. Org. Chem. 2002, 67, 2960-2969.
M. J. O'Donnell and F. Delgado "Enantiomeric enrichment of α-amino acid derivatives: recrystallization of N-Fmoc α-amino acid tert-butyl esters" Tetrahedron 2001, 57, 6641-6650.
W. L. Scott, F. Delgado, K. Lobb, R. S. Pottorf and M. J. O'Donnell "Solid-phase synthesis of amino amides and peptide amides with unnatural side chains" Tetrahedron Lett. 2001, 42, 2073-2076.
M. J. O'Donnell, F. Delgado, E. Domínguez, J. de Blas and W. L. Scott "Enantioselective solution- and solid-phase synthesis of glutamic acid derivatives via Michael addition reactions" Tetrahedron: Asymmetry 2001, 12, 821-828.
M. J. O'Donnell "The preparation of optically active α-amino acids from the benzophenone imines of glycine derivatives" Aldrichimica Acta 2001, 34, 3-15.
M. J. O'Donnell and W. L. Scott "Unnatural amino acid and peptide synthesis" in: Peptides 2000, J. Martinez and J.-A. Fehrentz, Eds., EDK: Paris, 2001, pp. 31-36.
M. J. O'Donnell "Asymmetric phase-transfer reactions" in: Catalytic Asymmetric Synthesis, Second Edition, I. Ojima, Ed., Wiley-VCH: New York, 2000, Chap. 10, pp 727-755.
M. J. O'Donnell, M. D. Drew, R. S. Pottorf and W. L. Scott "UPS on Weinreb resin: A facile solid-phase route to aldehyde and ketone derivatives of "unnatural" amino acids and peptides" J. Comb. Chem. 2000, 2, 172-181.
