A homo [3 + 2] dipolar cycloaddition: The reaction of nitrones with cyclopropanes

Angewandte Chemie - International Edition

Volumn 42, Issue 26, 2003, Pages 3023-3026

  Young, Ian S ^a   Kerr, Michael A ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

Cycloaddition; Cycloalkanes; Heterocycles; Nitrones

Indexed keywords

CATALYSTS; ESTERS; PROPANE;

DIASTEREOSELECTIVITY;

REACTION KINETICS;

CYCLOPROPANE DERIVATIVE; NITRONE; TETRAHYDRO 1,2 OXAZINE DERIVATIVE; UNCLASSIFIED DRUG; YTTERBIUM;

ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; CYCLOPROPANATION; DIASTEREOISOMER; STEREOCHEMISTRY;

EID: 0041806585     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351573     Document Type: Article

References (41)

1. a) 1,3-Dipolar Cycloaddition Chemistry, Vol. 1 (Ed. A. Padwa), Wiley, New York, 1984;
2. b) R. Huisgen in Advances in Cycloaddition, Vol. 1, (Ed.: D. P. Curran), JAI Press Inc., Greenwich, 1988, pp. 1-32;
3. c) P. Deshong, S. W. Lander, Jr., J. M. Leginus, C. M. Dicken in Advances in Cycloaddition, Vol. 1, (Ed.: D. P. Curran), JAI Press Inc., Greenwich, 1988, pp. 87-128;
4. d) A. Padwa in Advances in Cycloaddition, Vol. 2, (Ed.: D. P. Curran), JAI Press Inc., Greenwich, 1990, pp. 1-91;
5. e) W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, 1990;
6. f) A. Padwa in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Flemming), Wiley, New York, 1991;
7. g) P. A. Wade in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Flemming), Wiley, New York, 1991;
8. h) R. Huisgen in 1,3-Dipolar Cycloaddition Chemistry, Vol. 1 (Ed.: A. Padwa), Wiley, New York, 1984, pp. 1-176;
9. i) K. V. Gothelf, K. A. Jorgensen. Chem. Rev. 1998, 98, 863;
10. j) S. Kanemasa, Synlett 2002, 1371;
11. k) K. V. Gothelf in Cycloaddition Reactions in Organic Synthesis (Eds.: S. Kobayashi and K. A. Jorgensen), Wiley-VCH, Weinheim, 2002,pp. 211-248;
12. l) S. Kanemasa in Cycloaddition Reactions in Organic Synthesis (Eds.: S. Kobayashi and K. A. Jorgensen), Wiley-VCH, Weinheim, 2002, pp. 249-300.
13. a) P. E. Harrington, M. A. Kerr, Tetrahedron Lett. 1997,38, 5949;
14. b) M. A. Kerr, R. G. Keddy, Tetrahedron Lett. 1999, 5671;
15. c) D. B. England, T. D. O. Kuss, R. G. Keddy, J. Org. Chem. 2001, 66, 4704;
16. d) D. B. England, T. K. Woo, M. A. Kerr, Can. J. Chem. 2001, 79, 992.
17. a) S. J. Danishefsky, Accts. Chem. Res. 1979,12, 66.
18. b) H. Kotsuki, K. Arimura, T. Maruzawa, R. Ohshima, Synlett 1999, 650;
19. c) E. J. Corey, T. Gant, Tetrahedron Lett. 1994, 35, 5373.
20. For an excellent review of the chemistry of related cyclopropanes see: H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151.
21. T. T. Tidwell in The Chemistry of the Cyclopropyl Group, part 1, (Ed.: Z. Rappoport), Wiley, New York, 1987.
22. It may be tempting to refer to this process as a [3+3] cycloaddition reaction, however since a methylene unit of the reacting cyclopropane is not electronically involved in the reaction, we prefer the designation "homo [3+2] cycloaddition".
23. The Reissig group has elegantly prepared 1,2-oxazines by the reaction of nitrones with lithiated allenes. See: R. Pulz, S. Cicchi, A. Brandi, H.-U. Reissig, Eur. J. Org. Chem. 2003, 1153, and references therein.
24. a) M. Iwani, S. Kiyoto, H. Terano, M. Kohsaka, H. Aoki, H. Imanaka, J. Antibiot. 1987, 40, 589;
25. b) S. Kiyoto, T. Shibata, M. Yamashita, T. Komori, M. Okuharq, H. Terano, M. Kohsaka, H. Aoki, H. Imanaka, J. Antibiot. 1987, 40, 594;
26. c) I. Uchida, S. Takase, H. Kayakiri, S. Kiyoto, M. Hashimoto, J. Am. Chem. Soc. 1987, 109, 4108.
27. V. Gautheron-Chapoulaud, S. U. Pandya, P. Cividino, G. Masson, S. Py, Y. Vallee, Synlett 2001, 1281.
28. E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1965, 87, 1353.
29. Ytterbium triflate has emerged as an excellent catalyst for a wide variety of synthetic transformations. For general references see a) S. Kobayashi in Lanthanides: Chemistry and Use in Organic Synthesis (Ed.: S. Kobayashi), Springer, New York, 1999, pp. 63-118; b) S. Kobayashi, M. Sugiura, H. Kitagawa, W. W. L. Lam, Chem. Rev. 2002, 102, 2227; c) R. W. Marshman, Aldrichimica Acta, 1995, 28, 77.
30. Ytterbium triflate has emerged as an excellent catalyst for a wide variety of synthetic transformations. For general references see a) S. Kobayashi in Lanthanides: Chemistry and Use in Organic Synthesis (Ed.: S. Kobayashi), Springer, New York, 1999, pp. 63-118; b) S. Kobayashi, M. Sugiura, H. Kitagawa, W. W. L. Lam, Chem. Rev. 2002, 102, 2227; c) R. W. Marshman, Aldrichimica Acta, 1995, 28, 77.
31. Ytterbium triflate has emerged as an excellent catalyst for a wide variety of synthetic transformations. For general references see a) S. Kobayashi in Lanthanides: Chemistry and Use in Organic Synthesis (Ed.: S. Kobayashi), Springer, New York, 1999, pp. 63-118; b) S. Kobayashi, M. Sugiura, H. Kitagawa, W. W. L. Lam, Chem. Rev. 2002, 102, 2227; c) R. W. Marshman, Aldrichimica Acta, 1995, 28, 77.
32. Racemic total syntheses: a) T. Fukuyama, L. Xu, S. Goto, J. Am. Chem. Soc. 1992, 114, 383;
33. b) J. M. Schkeryantz, S. J. Danishefsky, J. Am. Chem. Soc. 1995, 117, 4722;
34. enantioselective total yntheses: c) T. Kato, E. Itoh, T. Yoshino, S. Terashima, Tetrahedron 1997, 53, 10229;
35. d) T. C. Judd, R. M. Williams, Angew. Chem. 2002, 114, 4877; Angew. Chem. Int. Ed. 2002, 41, 4683;
36. d) T. C. Judd, R. M. Williams, Angew. Chem. 2002, 114, 4877; Angew. Chem. Int. Ed. 2002, 41, 4683;
37. e) M. Suzuki, J. Kambe, H. Tokuyama, T. Fukuyama, Angew. Chem. 2002, 114, 4880; Angew. Chem. Int. Ed. 2002, 41, 4686;
38. e) M. Suzuki, J. Kambe, H. Tokuyama, T. Fukuyama, Angew. Chem. 2002, 114, 4880; Angew. Chem. Int. Ed. 2002, 41, 4686;
39. for a synthesis of related racemic FR-66979 see: f) R. Ducray, M. A. Ciufolini, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.
40. for a synthesis of related racemic FR-66979 see: f) R. Ducray, M. A. Ciufolini, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.
41. S. Kobayashi, M. Kawamura, J. Am. Chem. Soc. 1998, 120, 5841.