Asymmetric tandem reactions based on nitroalkenes: a one-pot construction of functionalized chiral bicycles by a three-component reaction

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Martín Avalos, Pedro Cintas, José L. Jiménez and Juan C. Palacios


Abstract

Asymmetric tandem cycloaddition of a chiral carbohydrate nitroalkene with ethyl vinyl ether in the presence of electron- withdrawing alkenes produces a facile assembly of bicyclic systems, which can further be selectively cleaved to give homologated carbohydrates.


References

  1. For reviews on tandem reactions: T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992 Search PubMed; L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131 Search PubMed; R. A. Bunce, Tetrahedron, 1995, 51, 13 103 CrossRef; J. D. Winkler, Chem. Rev., 1996, 96, 167 CrossRef CAS.
  2. For a review on tandem cycloadditions of nitroalkenes: S. E. Denmark and A. Thorarensen, Chem. Rev., 1996, 96, 137 Search PubMed.
  3. M. Avalos, R. Babiano, P. Cintas, F. J. Higes, J. L. Jiménez, J. C. Palacios and M. A. Silva, J. Org. Chem., 1996, 61, 1880 CrossRef CAS.
  4. R. N. Butler, D. Cunningham, E. G. Marren, P. McArdle and D. F. O'Shea, J. Chem. Res. (S), 1992, 256 Search PubMed.
  5. For reviews on branched and higher carbon sugars: J. Yoshimura, Adv. Carbohydr. Chem. Biochem., 1984, 42, 69 Search PubMed; A. Zamojski and S. Jarosz, Pol. J. Chem., 1992, 66, 525 Search PubMed.
  6. A general route for the homologation-amination of aldehydes by addition of sugar nitrones to metalated thiazoles has been recently devised: A. Dondoni, S. Franco, F. Junquera, F. L. Merchán, P. Merino, T. Tejero and V. Bertolasi, Chem. Eur. J., 1995, 1, 505 Search PubMed and references cited therein A. Dondoni, F. Junquera, F. L. Merchán, P. Merino, M.-C. Scherrmann and T. Tejero, J. Org. Chem., 1997, 62, 5484 CAS.
  7. For reviews on syntheses of isoxazolines by inter- and intramolecular 1,3-dipolar cycloadditions, see A. Padwa, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and M. F. Semmelhack, Pergamon, Oxford, 1991, vol. 4, pp. 1069–1109 Search PubMed; P. A. Wade, ibid, vol. 4, pp. 1111–1168 Search PubMedFor a review on chiral isoxazolines: B. H. Kim and D. P. Curran, Tetrahedron, 1993, 49, 293 Search PubMed; For the formation of aldol-type products by ring-cleavage of isoxazolines: W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, 1990, p. 293 Search PubMed.
  8. The reduced chiral systems, optically active isoxazolidines, can also be utilized in organic synthesis: M. Frederickson, Tetrahedron, 1997, 53, 403 Search PubMed.
  9. K. Undheim, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon, Oxford, 1984, vol. 6, pp. 632–633 Search PubMed.
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