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The Scientific World Journal
Volume 2012, Article ID 643647, 10 pages
http://dx.doi.org/10.1100/2012/643647
Research Article

The Chemoselective Reduction of Isoxazoline γ-Lactams Through Iminium Aza-Diels-Alder Reactions: A Short-Cut Synthesis of Aminols as Valuable Intermediates towards Nucleoside Derivatives

Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy

Received 27 December 2011; Accepted 16 January 2012

Academic Editors: S. De la Moya Cerero and G. B. Shul'pin

Copyright © 2012 Misal Giuseppe Memeo et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. B. Olofsson and P. Somfai, “Determination of the relative configuration of vic-amino alcohols,” Tetrahedron Letters, vol. 44, no. 6, pp. 1279–1281, 2003. View at Publisher · View at Google Scholar
  2. S. Kobayashi, H. Ishitani, and M. Ueno, “Catalytic asymmetric synthesis of both syn- and anti-β-amino alcohols,” Journal of the American Chemical Society, vol. 120, no. 2, pp. 431–432, 1998. View at Publisher · View at Google Scholar
  3. D. J. Ager, I. Prakash, and D. R. Schaad, “1,2-amino al-cohols and their heterocyclic derivatives as chiral aux-iliaries in asymmetric synthesis,” Chemical Reviews, vol. 96, no. 2, pp. 835–876, 1996. View at Google Scholar
  4. A. Berkessel and R. Riedl, “Fluorescence reporters for phosphodiesterase activity,” Angewandte Chemie, vol. 36, no. 13-14, pp. 1481–1483, 1997. View at Google Scholar
  5. G. Desimoni, G. Faita, and P. Quadrelli, “Pyridine-2,6-bis(oxazolines), helpful ligands for asymmetric catalysts,” Chemical Reviews, vol. 103, no. 8, pp. 3119–3154, 2003. View at Publisher · View at Google Scholar
  6. G. Desimoni, G. Faita, and K. A. Jorgensen, “C2-symmetric chiral bis(oxazoline) ligands in asymmetric catalysis,” Chemical Reviews, vol. 106, no. 9, pp. 3561–3651, 2006. View at Publisher · View at Google Scholar
  7. B. S. Bodnar and M. J. Miller, “The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses,” Angewandte Chemie, vol. 50, no. 25, pp. 5630–5647, 2011. View at Publisher · View at Google Scholar
  8. P. F. Vogt and M. J. Miller, “Development and applications of amino acid-derived chiral acylnitroso hetero Diels-Alder reactions,” Tetrahedron, vol. 54, no. 8, pp. 1317–1348, 1998. View at Publisher · View at Google Scholar
  9. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, San Diego, Calif, USA, 1987.
  10. P. Quadrelli, M. Mella, P. Paganoni, and P. Caramella, “Cycloadditions of nitrile oxides to the highly reactive N-acyl-2-oxa-3- azanorborn-5-enes afford versatile cycloadducts and a convenient entry to highly functionalized derivatives,” European Journal of Organic Chemistry, no. 14, pp. 2613–2620, 2000. View at Google Scholar
  11. P. Quadrelli, V. Fassardi, A. Cardarelli, and P. Caramella, “Intra- and intermolecular hydrogen bonding effects in cycloadditions between nitrile oxides and 4-benzoylamino-2-cyclopenten-1-ol and its derivatives,” European Journal of Organic Chemistry, no. 13, pp. 2058–2065, 2002. View at Google Scholar
  12. P. Quadrelli, A. G. Invernizzi, and P. Caramella, “A mild oxidation of nitrile oxides: a new synthetic route to nitroso carbonyl intermediates,” Tetrahedron Letters, vol. 37, no. 11, pp. 1909–1912, 1996. View at Publisher · View at Google Scholar
  13. P. Quadrelli, M. Mella, A. G. Invernizzi, and P. Caramella, “The mild oxidation of nitrile oxides affords a convenient entry to nitrosocarbonyl intermediates, versatile tools in organic syntheses,” Tetrahedron, vol. 55, no. 34, pp. 10497–10510, 1999. View at Publisher · View at Google Scholar
  14. P. Quadrelli, A. Piccanello, N. V. Martinez, B. Bovio, M. Mella, and P. Caramella, “Isoxazoline-carbocyclic aminols for nucleoside synthesis through aza-Diels-Alder reactions,” Tetrahedron, vol. 62, no. 31, pp. 7370–7379, 2006. View at Publisher · View at Google Scholar · View at Scopus
  15. P. A. Grieco and S. D. Larsen, “Iminium ion-based Diels–alder reactions: N-benzyl-2-azanorbornene [2-Azabicyclo[2.2.1]hept-5-ene, 2-(phenylmethyl)-],” Organic Syntheses, vol. 68, p. 206, 1990. View at Google Scholar
  16. X. Sauvage and L. Delaude, “The synthesis of N-benzyl-2-azanorbornene via aqueous hetero Diels-Alder reaction. An undergraduate project in organic synthesis and structural analysis,” Journal of Chemical Education, vol. 85, no. 11, pp. 1538–1540, 2008. View at Google Scholar
  17. P. A. Grieco and A. Bahsas, “Immonium ion based synthetic methodology: a novel method for the N-methylation of dipeptides and amino acid derivatives via retro aza Diels-Alder reactions,” Journal of Organic Chemistry, vol. 52, no. 26, pp. 5746–5749, 1987. View at Google Scholar
  18. S. D. Larsen and P. A. Grieco, “Aza Diels-Alder reactions in aqueous solution: cyclocondensation of dienes with simple iminium salts generated under Mannich conditions,” Journal of the American Chemical Society, vol. 107, no. 6, pp. 1768–1769, 1985. View at Google Scholar
  19. J. E. Rodriguez-Borges, X. Garcia-Mera, F. Fernandez, V. H. C. Lopez, A. L. Magolhaes, and M. N. D. S. Cordeiro, “Expermintal AND dft study of the aza-diels-alder reaction between cyclopentadiene AND protoned benzylimine derivated from glyoxylates,” Tetrahedron, vol. 61, no. 46, pp. 10951–10957, 2005. View at Google Scholar
  20. D. G. Lynn, K. Jaffe, M. Cornwall, and W. Tramontano, “Characterization of an endogenous factor controlling the cell cycle of complex tissues,” Journal of the American Chemical Society, vol. 109, no. 19, pp. 5858–5859, 1987. View at Google Scholar
  21. P. A. Grieco, S. D. Larsen, and W. F. Fobare, “Aza Diels-Alder reactions in water: cyclocondensation of C-acyl iminium ions with cyclopentadiene,” Tetrahedron Letters, vol. 27, no. 18, pp. 1975–1978, 1986. View at Google Scholar
  22. D. A. Alonso, S. K. Bertilsson, S. Y. Johnsson, S. J.M. Nordin, M. J. Södergren, and P. G. Andersson, “New expedient route to both enantiomers of nonproteinogenic α-amino acid derivatives from the unsaturated 2-aza-bicyclo moiety,” Journal of Organic Chemistry, vol. 64, no. 7, pp. 2276–2280, 1999. View at Publisher · View at Google Scholar
  23. P. D. Bailey, R. D. Wilson, and G. R. Brown, “Stereoselective synthesis of pipecolic acid derivatives using a aza-Diels-Alder reactions,” Tetrahedron Letters, vol. 30, no. 48, pp. 6781–6784, 1989. View at Publisher · View at Google Scholar
  24. H. Waldman, “Reactivity of tri-tert-butylazete,” Angewandte Chemie International Edition in English, vol. 27, no. 2, pp. 272–274, 1988. View at Publisher · View at Google Scholar
  25. H. Abraham and L. Stella, “Reaction d'aza-diels-alder diastereoselective: utilisation de la 1-phenylethyl imine de glyoxylated d'alkyle pour la synthese de derives d'α-amino acides cycliques,” Tetrahedron, vol. 48, no. 44, pp. 9707–9718, 1992. View at Publisher · View at Google Scholar
  26. L. Stella and H. Abraham, “Asymmetric Aza-Diels-Alder reaction using the chiral 1-phenyl-ethyl imine of methyl glyoxylate,” Tetrahedron Letters, vol. 31, p. 2603, 1990. View at Google Scholar
  27. H. Böhme, K. Hartke, and A. Müller, “Über α-halogenierte amine, XII. α-halogenierte amine als dienophile verbindungen,” Chemische Berichte, vol. 96, no. 2, pp. 607–608, 1963. View at Publisher · View at Google Scholar
  28. D. S. Grierson and H. P. Husson, “Heteroatom manipulation,” in Comprehensive Organic Synthesis, B. M. Trost and I. Fleming, Eds., vol. 6, pp. 909–947, Pergamon Press, Oxford, UK, 1991. View at Google Scholar
  29. R. Michelot, “Etude du mecanisme de le reaction de Polonovski, influence de la structure de l'oxyde d'amine sur le deroulement de la reaction,” Bulletin de la Société Chimique de France, p. 4377, 1969. View at Google Scholar
  30. P. Quadrelli, B. Bovio, A. Piccinini, P. Caramella, F. de Sarlo, and F. Machetti, “Conversion of a nitrosocarbonyl hetero Diels-Alder cycloadduct to useful isoxazoline-carbocyclic aminols,” Tetrahedron, vol. 65, no. 51, pp. 10679–10684, 2009. View at Publisher · View at Google Scholar
  31. P. Quadrelli, A. Piccanello, M. Mella, A. Corsaro, and V. Pistarà, “From cyclopentadiene to isoxazoline-carbocyclic nucleosides: a rapid access to biological molecules through aza-Diels-Alder reactions,” Tetrahedron, vol. 64, no. 16, pp. 3541–3547, 2008. View at Publisher · View at Google Scholar
  32. C. Djerassi and R. R. Engle, “Oxidations with ruthenium tetroxide,” Journal of the American Chemical Society, vol. 75, no. 15, pp. 3838–3840, 1953. View at Google Scholar · View at Scopus
  33. B. Plietker, “Selectivity versus reactivity-recent advances in RuO4 catalyzed oxidations,” Synthesis, no. 15, Article ID E13405SS, pp. 2453–2472, 2005. View at Publisher · View at Google Scholar · View at Scopus
  34. H. Petride, O. Costan, C. Draghici, C. Florea, and A. Petride, “RuO4-Mediated oxidation of N-benzylated tertiary amines. 2. Regioselectivity for N,N-dimethyl- and N,N-diethylbenzylamine as substrates,” Arkivoc, vol. 2005, no. 10, pp. 18–32, 2005. View at Google Scholar
  35. H. Petride, C. Draghici, C. Florea, and A. Petride, “RuO4-mediated oxidation of N-benzylated tertiary amines. Are amine N-oxides and iminium cations reactions intermediates?” Central European Journal of Chemistry, vol. 2, no. 2, pp. 302–322, 2004. View at Publisher · View at Google Scholar
  36. M. G. Memeo, B. Bovio, and P. Quadrelli, “RuO4-catalyzed oxidation reactions of isoxazolino-2-azanorbornane derivatives: a short-cut synthesis of tricyclic lactams and peptidomimetic γ-amino acids,” Tetrahedron, vol. 67, no. 10, pp. 1907–1914, 2011. View at Google Scholar
  37. P. Caramella and P. Grünanger, “Nitrile oxides and imines,” in 1,3-Dipolar Cycloaddition Chemistry, A. Padwa, Ed., vol. 1, pp. 291–392, Wiley, New York, NY, USA, 1984. View at Google Scholar
  38. A. Piperno, U. Chiacchio, D. Iannazzo, S. V. Giofrè, G. Romeo, and R. Romeo, “First example of direct RuO4-catalyzed oxidation of isoxazolidines to 3-isoxazolidones,” Journal of Organic Chemistry, vol. 72, no. 10, pp. 3958–3960, 2007. View at Publisher · View at Google Scholar
  39. P. H. J. Carlsen, T. Katsuki, V. S. Martin, and K. B. Sharpless, “A greatly improved procedure for ruthenium tetroxide catalyzed oxidations of organic compounds,” Journal of Organic Chemistry, vol. 46, no. 19, pp. 3936–3938, 1981. View at Publisher · View at Google Scholar
  40. M. Kaname and S. Yoshifuji, “First synthesis of lycoperdic acid,” Tetrahedron Letters, vol. 33, no. 52, pp. 8103–8104, 1992. View at Publisher · View at Google Scholar
  41. S. Yoshifuji and M. Kaname, “Asymmetric synthesis of lycoperdic acid,” Chemical and Pharmaceutical Bulletin, vol. 43, no. 10, pp. 1617–1620, 1995. View at Google Scholar
  42. P. Merino, J. Revuelta, T. Tejero et al., “Enantioselective synthesis of 4-hydroxy-D-pyroglutamic acid derivatives by an asymmetric 1,3-dipolar cycloaddition,” Tetrahedron Asymmetry, vol. 13, no. 2, pp. 167–172, 2002. View at Publisher · View at Google Scholar
  43. S. M. Daluge, M. T. Martin, B. R. Sickles, and D. A. Livingston, “An efficient, scalable synthesis of the HIV reverse transcriptase inhibitor Ziagen® (1592U89),” Nucleosides, Nucleotides and Nucleic Acids, vol. 19, no. 1-2, pp. 297–327, 2000. View at Google Scholar · View at Scopus
  44. N. M. Yoon, C. S. Pak, H. C. Brown, S. Krishnamurthy, and T. P. Stocky, “Selective reductions. XIX. Rapid reaction of carboxylic acids with borane-tetrahydrofuran. Remarkably convenient procedure for the selective conversion of carboxylic acids to the corresponding alcohols in the presence of other functional groups,” Journal of Organic Chemistry, vol. 38, no. 16, pp. 2786–2792, 1973. View at Publisher · View at Google Scholar
  45. J. V. B. Kanth and M. Periasamy, “Selective reduction of carboxylic acids into alcohols using NaBH4 and I2,” Journal of Organic Chemistry, vol. 56, no. 20, pp. 5964–5965, 1991. View at Google Scholar · View at Scopus
  46. P. Grünanger and P. V. Finzi, Isoxazoles, John Wiley & Sons, New York, NY, USA, 1991.
  47. R. Huisgen, P. H. J. Ooms, M. Mingin, and N. L. Allinger, “Exceptional reactivity of the bicyclo[2.2.1]heptene double bond,” Journal of the American Chemical Society, vol. 102, no. 11, pp. 3951–3953, 1980. View at Publisher · View at Google Scholar
  48. N. G. Rondan, M. N. Paddon-Row, P. Caramella, and K. N. Houk, “Nonplanar alkenes and carbonyls: a molecular distortion which parallels addition stereoselectivity,” Journal of the American Chemical Society, vol. 103, no. 9, pp. 2436–2438, 1981. View at Google Scholar
  49. P. Caramella, N. G. Rondan, M. N. Paddon-Row, and K. N. Houk, “Origin of π-facial stereoselectivity in additions to π-bonds: generality of the anti-periplanar effect,” Journal of the American Chemical Society, vol. 103, no. 9, pp. 2438–2440, 1981. View at Google Scholar
  50. K. N. Houk, N. G. Rondan, F. K. Brown, W. L. Jorgensen, J. D. Madura, and D. C. Spellmeyer, “The origin and consequences of alkene pyramidalization in ground and triplet excited states,” Journal of the American Chemical Society, vol. 105, no. 19, pp. 5980–5988, 1983. View at Publisher · View at Google Scholar
  51. M. G. Memeo, D. Mantione, B. Bovio, and P. Quadrelli, “RuO4-catalyzed oxidation reactions of N-alkylisoxazolino-2- azanorbornane derivatives: an expeditious route to tricyclic γ-lactams,” Synthesis, no. 13, pp. 2165–2174, 2011. View at Publisher · View at Google Scholar
  52. J. M. Bakke and A. E. Frøhaug, “Ruthenium tetraoxide mediated reactions: the mechanisms of oxidations of hydrocarbons and ethers,” Journal of Physical Organic Chemistry, vol. 9, no. 6, pp. 310–318, 1996. View at Google Scholar
  53. J. M. Bakke and A. E. Frøhaug, “Mechanism of RuO4-mediated oxidations of saturated hydrocarbons, isotope effects, solvent effects and substituent effects,” Journal of Physical Organic Chemistry, vol. 9, no. 7, pp. 507–513, 1996. View at Google Scholar
  54. J. M. Bakke and J. E. Braenden, “Derivatisation of saturated hydrocarbons. The mechanism RuO4 Oxidation,” Acta Chemica Scandinavica, vol. 45, no. 4, pp. 418–423, 1991. View at Google Scholar
  55. T. Naota, H. Takaya, and S. L. Murahashi, “Ruthenium-catalyzed reactions for organic synthesis,” Chemical Reviews, vol. 98, no. 7, pp. 2599–2660, 1998. View at Google Scholar · View at Scopus
  56. A. E. Shilov and G. B. Shul'pin, “Activation of C-H bonds by metal complexes,” Chemical Reviews, vol. 97, no. 8, pp. 2879–2932, 1997. View at Publisher · View at Google Scholar
  57. G. Lin, K. K. Midha, and E. M. Hawes, “Synthesis of the piperidinone metabolites of piperidine type phenothiazine antipsychotic drugs via ruthenium tetroxide oxidation,” Journal of Heterocyclic Chemistry, vol. 28, no. 2, pp. 215–219, 1991. View at Google Scholar · View at Scopus
  58. J. Zabicky, The Chemistry of Amides, John Wiley & Sons, London, UK, 1970.
  59. N. G. Gaylord, Reduction with Complex Metal Hydrides, Intersceince Publishers, New York, NY, USA, 1956.
  60. J. R. Malpass and N. J. Tweddle, “Reaction of chlorosulphonyl isocyanate with 1,3-dienes. Control of 1,2-and 1,4-addition pathways and the synthesis of aza- and oxa-bicyclic systems,” Journal of the Chemical Society, Perkin Transactions, no. 8, pp. 874–883, 1977. View at Google Scholar