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Professor Scott Eric Denmark
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Publications

Nitroalkene and Related Cycloaddition (Including Tandem)

  1. alpha -Chloro Ketoximes as Precursors of Nitrosoalkenes: Preparation, Stereochemistry, and Conformation (with M. S. Dappen) J. Org. Chem. 1984, 49, 798-806.[pdf]
     
  2. Intramolecular [4+2] Cycloadditions of Nitrosoalkenes with Olefins (with M. S. Dappen and J. A. Sternberg) J. Org. Chem. 1984, 49, 4741-4743.[pdf]
     
  3. Intramolecular [4+2] Cycloadditions of Nitroalkenes with Olefins (with M. S. Dappen and C. J. Cramer) J. Am. Chem. Soc. 1986, 108, 1306-1307.[pdf]
     
  4. Intermolecular [4+2]-Cycloadditions of Nitroalkenes with Cyclic Olefins. Transformations of Cyclic Nitronates (with C. J. Cramer and J. A. Sternberg) Helv. Chim. Acta 1986, 69, 1971-1989.[pdf]
     
  5. Intramolecular [4+2]-Cycloadditions of Vinylnitrosonium Cations with Olefins (with C. J. Cramer and M. S. Dappen) J. Org. Chem. 1987, 52, 877-887.[pdf]
     
  6. Tandem [4+2]/[3+2]-Cycloadditions: Facile and Stereoselective Construction of Polycyclic Frameworks (with Y.-C. Moon and C. B. W. Senanayake) J. Am. Chem. Soc. 1990, 112, 311-316.[pdf]
     
  7. Tandem [4+2]/[3+2]-Cycloadditions. 2. Asymmetric Induction with a Chiral Vinyl Ether (with C. B. W. Senanayake and G.-D. Ho) Tetrahedron 1990, 46, 4857-4876.[pdf]
     
  8. Intramolecular [4+2]-Cycloaddition of Nitroalkenes with Olefins. 2 (with Y.-C. Moon, C. J. Cramer, M. S. Dappen and C. B. W. Senanayake) Tetrahedron1990, 46, 7373-7392.[pdf]
     
  9. Tandem Inter [4+2] / Intra [3+2]-Cycloadditions. 3. The Stereochemical Influence of the Lewis Acid (with M. E. Schnute) J. Org. Chem. 1991, 56, 6738-6739.[pdf]
     
  10. Inter- and Intramolecular [4+2]-Cycloadditions of Nitroalkenes with Olefins. 2-Nitrostyrenes (with B. S. Kesler and Y.-C. Moon) J. Org. Chem. 1992, 57, 4912-4924.[pdf]
     
  11. The Tandem Cycloaddition Chemistry of Nitroalkenes (with M. E. Schnute, C. B. W. Senanayake, Y.-C. Moon and D. S. Middleton) Proceedings of the 5th International Kyoto Conference on New Aspects of Organic Chemistry; Z.-I. Yoshida and Y. Ohshiro, Eds.; Kodansha Press, 1992, pp. 215-239.[pdf]
     
  12. Tandem Inter [4+2]/Intra [3+2]-Cycloadditions. 4. Cycloadditions with E- and Z-1-Propenyl Ethers (with C. B. W. Senanayake) J. Org. Chem. 1993, 58, 1853-1858.[pdf]
     
  13. Tandem Inter [4+2] / Intra [3+2]-Cycloadditions. 5. Origin of the Lewis Acid Dependent Reversal of Stereoselectivity (with M. E. Schnute and C. B. W. Senanayake) J. Org. Chem. 1993, 58, 1859-1874.[pdf]
     
  14. A General Method for the Preparation of 2,2-Disubstituted 1-Nitroalkenes (with L. R. Marcin) J. Org. Chem. 1993, 58, 3850-3856.[pdf]
     
  15. Nitroalkene [4+2] Cycloaddition as a General and Stereoselective Route to 3,3- and 3,4-Disubstituted Pyrrolidines (with L. R. Marcin) J. Org. Chem. 1993, 58 , 3857-3868.[pdf]
     
  16. Nitroalkene [4+2] Cycloadditions with 2-Acyloxyvinyl Ethers. Stereoselective Synthesis of 3-Hydroxy-4-Substituted Pyrrolidines (with M. E. Schnute) J. Org. Chem. 1994, 59 4576-4595.[pdf]
     
  17. The Tandem Cycloaddition Chemistry of Nitroalkenes. A Novel Synthesis of (-)-Hastanecine (with A. Thorarensen) J. Org. Chem. 1994, 59, 5672-5680.[pdf]
     
  18. The Tandem Cycloaddition Chemistry of Nitroalkenes (with M. E. Schnute, A. Thorarensen, D. S. Middleton and A. Stolle) Pure Appl. Chem. 1994, 66, 2041-2044.[pdf]
     
  19. Tandem Inter [4+2]/;Intra [3+2] Cycloadditions. 6. The Bridged Mode (with A. Stolle, J. A. Dixon and V. Guagnano) J. Am. Chem. Soc. 1995, 117, 2100-2101.[pdf]
     
  20. Nitroalkene Inter [4+2]/Intra [3+2] Tandem Cycloadditions. 7. Application of (R)-(–)-2,2-Diphenylcyclopentanol as the Chiral Auxiliary (with M. E. Schnute, L. R. Marcin, and A. Thorarensen) J. Org. Chem. 1995, 60, 3205-3220.[pdf]
     
  21. Asymmetric Nitroalkene [4+2] Cycloadditions:Enantioselective
    Synthesis of 3- and 3,4-Substituted Pyrrolidines (with L. R. Marcin) J. Org. Chem. 1995, 60, 3221-3235.[pdf]
     
  22. A General Strategy for the Synthesis of Cis-Substituted Pyrrolizidine Bases. The Synthesis of (-)-Rosmarinecine (with A. Thorarensen and D. S. Middleton) J. Org. Chem. 1995, 60, 3574-3575.[pdf]
     
  23. Tandem [4+2]/[3+2] Cycloadditions of Nitroalkenes (with A. Thorarensen) Chem. Rev. 1996, 96, 137-165.[pdf]
     
  24. Tandem Inter [4+2]/Intra [3+2] Cycloadditions. 8. Unactivated Dipolarophiles (with C. B. W. Senanayake) Tetrahedron 1996, 52, 11579-11600.[pdf]
     
  25. Tandem [4+2]/[3+2] Cycloadditions of Nitroalkenes. 9. The Synthesis of (-)-Rosmarinecine (with A. Thorarensen and D. S. Middleton) J. Am. Chem. Soc. 1996, 118, 8266-8277.[pdf]
     
  26. Tandem [4+2]/[3+2] Cycloadditions of Nitroalkenes. 10. trans-2-(1-Methyl-1-Phenylethyl)-cyclohexanol as a New Auxiliary (with A. Thorarensen) J. Org. Chem. 1996, 61, 6727-6729.[pdf]
     
  27. (2aS, 3S, 6S, 7S, 7bR)-7-[(Dimethylphenyl)-silyl]-2-oxo-6-[(1R,2S)-2-phenylcyclo-hexyloxy]-2a,3,6,7,7a,7b-hexahydro-2-1.4.5-trioxa-4a-azaxyxlopenta[cd]indene-3-carboxylic Acid 1-Methyethyl Ester (with A.Thorarensen and K. A. Swiss) Acta Cryst C. 1996, C52, 2558-2561.[pdf]
     
  28. rel-(1R. 6S, 7S, 8R, 9S)-9-Methyl-8-phenyl-6-[1(1S.2R)-(2-
    phenylcyclohexyl)oxy]-4-aza-3,5-dioxatricyclo[5.2.1.0 4,9]decane (with K. A. Swiss and J. A. Dixon) Acta Cryst C. 1996, C52, 2561-2563.[pdf]
     
  29. Tandem Inter [4+2]/Intra [3+2] Cycloadditions. 11. The Synthesis of (+)-Crotanecine (with A. Thorarensen) J. Am. Chem. Soc. 1997, 119, 125-137.
    [pdf]
     
  30. Tandem [4+2]/[3+2] Cycloadditions of Nitroalkenes. 12. Synthesis of (–)-Platynecine (with D. L. Parker and J. A. Dixon) J. Org. Chem. 1997, 62, 435-436.[pdf]
     
  31. Tandem [4+2]/[3+2] Cycloadditions of Nitroalkenes. 13. The Synthesis of (+)-Detoxinine (with A. R. Hurd and H. Sacha) J. Org. Chem. 1997, 62, 1668-1674.[pdf]
     
  32. Asymmetric Construction of a Quaternary Carbon Center by Tandem [4+2]/[3+2] Cycloadditions of Nitroalkenes. The Total Synthesis of (–)-Mesembrine (with L. R. Marcin) J. Org. Chem. 1997, 62, 1675-1686.[pdf]
     
  33. Tandem Inter [4+2] / Intra [3+2] Cycloadditions of Nitroalkenes. 15. The Bridged Mode alpha-Tether (with V. Guagnano, J. A. Dixon and A. Stolle) J. Org. Chem. 1997, 62, 4610-4628.[pdf]
     
  34. Tandem Inter [4+2]/Intra [3+2] Cycloadditions of Nitroalkenes. A Versatile Asymmetric Synthesis of Highly Functionalized Aminocyclopentanes (with J. A. Dixon) J. Org. Chem. 1997, 62, 7086-7087.
    [pdf]
     
  35. Tandem Inter [4+2]/Intra [3+2] Cycloadditions. 17. The Spiro Mode. Efficient and Highly Selective Synthesis of Azapropellanes (with D. S. Middleton) J. Org. Chem, 1998, 63, 1604-1618.[pdf]
     
  36. Tandem Inter [4+2]/Intra [3+2] Cycloadditions with Nitroethylene(with A. R. Hurd) J. Org. Chem. 1998, 63, 3045-3050.[pdf]
     
  37. The Synthesis of (1R,2R,3R,7R,7aR)-Hexahydro-3 (hydroxymethyl)-1H-pyrrolizine-1,2,7-triol, "7-Epiaustraline" (with B. Herbert) J. Am. Chem. Soc . 1998 , 116, 7357-7358.[pdf]
     
  38. Tandem Inter [4+2]/Intra [3+2] Cycloadditions of Nitroalkenes. The Bridged Mode beta-Tether (with J. A. Dixon) J. Org. Chem. 1998, 63, 6167-6177.
    [pdf]
     
  39. Tandem Inter [4+2]/Intra [3+2] Cycloadditions of Nitroalkenes. Asymmetric Synthesis of Highly Functionalized Aminocyclopentanes Using the Bridged Mode beta-Tether Process. (with J. A. Dixon) J. Org. Chem. 1998, 63, 6178-6195.[pdf]
     
  40. The Tandem Cycloaddition Chemistry of Nitroalkenes: Preparative and Theoretical Studies on the Stereochemical Course of [3+2]-Cycloaddition of Cyclic Nitronates (with M. J. Seierstad and B. Herbert) J. Org. Chem. 1999, 64, 884-901.[pdf]
     
  41. The Tandem Cycloaddition Chemistry of Nitroalkenes: Further Studies on the Stereochemical Influence of the Lewis Acid (with M. Seierstad) J. Org. Chem. 1999, 64, 1610-1619.[pdf]
     
  42. Enantioselective Total Syntheses of (+)-Castanospermine, (+)-6-Epicastanospermine, (+)-Australine, and (+)-3-Epiaustraline (with E. A. Martinborough) J. Am. Chem. Soc. 1999, 121, 3046-3056.[pdf]
     
  43. Synthesis of (+)-Casuarine (with A. R. Hurd) Org. Lett. 1999, 1, 1311-1314.[pdf]
     
  44. Synthesis of (+)-Casuarine (with A. R. Hurd) J. Org. Chem.2000, 65, 2875-2886.[pdf]
     
  45. Synthesis of (–)-7-Epiaustraline and (–)-1-Epicastanospermine (with B. Herbert) J. Org. Chem. 2000, 65, 2887-2896.[pdf]
     
  46. Synthesis of (+)-1- Epiaustraline (with J. J. Cottell) J. Org. Chem. 2001, 66, 4276-4284.[pdf]
     
  47. Tandem Double Intramolecular [4+2]/[3+2] Cycloadditions of Nitroalkenes (with L. Gomez) Org. Lett. 2001, 3, 2907-2910.[pdf]
     
  48. Studies on the Reduction and Hydrolysis of Nitroso Acetals (with V. Guagnano and J. Vaugeois) Can. J. Chem. 2001, 79, 1606-1616.[pdf]
     
  49. Synthesis of cis,cis,cis,cis-[5.5.5.5]-1-Azafenestrane (with L. A. Kramps and J. Montgomery) Angew. Chem. Int. Ed. 2002, 41, 4122-4125.[pdf]
     
  50. Inter- and Intramolecular [4+2] Cycloaddition of Nitroalkenes with Allenylsilanes. A Case of Unexpected Regioselectivity (with L. Gomez) Heterocycles 2002, 58, 129-136.[pdf]
     
  51. Tandem Inter [4+2]/Intra [3+2] Cycloadditions of Nitroalkenes. Application to the Synthesis of Aminocarbasugars (with M. Juhl) Helv. Chim. Acta 2002, 85, 3712-3736.[pdf]
     
  52. Tandem Double Intramolecular [14+2]/[3+2] Cycloadditions of Nitroalkenes. The Fused/Bridged Mode. (with L. Gomez) J. Org. Chem. 2003, 68, 8015-8024.[pdf]
     
  53. 2-Silyloxy-1,2-oxazines, a New Type of Acetals of Conjugated Nitroso Alkenes (with A. A. Tishkov, A. V. Lesiv, Y. A. Khomutova, Y. A. Strelenko, I. D. Nesterov, M. Y. Antipin, Ioffe, S.) J. Org. Chem. 2003, 68, 9477-9480.[pdf]
     
  54. Synthesis of cis,cis,cis,cis-[5.5.5.4]-1-Azafenestrane with Discovery of an Unexpected Dyotropic Rearrangement (with J. I. Montgomery) Angew. Chem. Int. Ed. 2005, 44, 3732-3736.[pdf]
     
  55. Intramolecular [4+2] Cycloaddition of Nitroalkenes for Construction of Vicinal Quarternary Stereocenters (with R. Baiazitov) Org. Lett. 2005, 7(25) 5617-5620.  [pdf]
     
  56. Tandem Double-Intramolecular [4+2]/[3+2] Cycloadditons of Nitroalkenes. Studies toward a Total Synthesis of Daphnilactone B: Piperidine Ring Construction (with R. Y. Baiazitov) J. Org. Chem.2006, 71, 593-605.  [pdf]
     
  57. A General Synthesis of N-Vinyl Nitrones (with J. I. Montgomery) J. Org. Chem. 2006, 71, 6211-6220. [pdf]
     
  58. Synthesis, X-Ray Crystallography and Computational Analysis of 1-Azafenestranes (with J. I. Montgomery and L. A. Kramps) J. Am. Chem. Soc. 2006, 128, 11620-11630. [pdf]
     
  59. A Tandem Nitroalkene Conjugate Addition/[3+2] Cycloaddition Approach to the Synthesis of the Pentacyclic Core of (±)-Scandine (with J. J. Cottell) Adv. Synth. Cat. 2006, 348, 2397-2402. [pdf]

  60. Lewis Acid-Promoted Conjugate Addition of Dienol Silyl Ethers to Nitroalkenes: Synthesis of 3-Substituted Azepanes (with M. Xie) J. Org. Chem. 2007, 72, 7050-7053. [pdf]
     
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