Generation of functionalized azomethine ylides and their application to stereoselective heterocycle synthesis: an equivalent process of C-unsubstituted nitrile ylide cycloaddition reaction

Tetrahedron

Volumn 63, Issue 7, 2007, Pages 1630-1643

  Kawashima, Keisuke ^a   Kakehi, Akikazu ^b   Noguchi, Michihiko ^a  

^a YAMAGUCHI UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^b SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE YLIDE; MALEIMIDE DERIVATIVE; PROLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 33846082694     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.004     Document Type: Article

References (50)

1. Obst U., Betschmann P., Lemer C., Seiler P., Diederich F., Gramilich V., Weber L., Banner D.W., and Schönholzer P. Helv. Chim. Acta 83 (2000) 855-909
2. Pearson W.H. In: Atta-Rahman (Ed). Studies in Natural Products Chemistry Vol. 1 (1998), Elsevier, New York, NY 322-358
3. Gribble G.W. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry Vol. 2 (1996), Pergamon, Oxford, UK 207-257
4. Grigg R., and Kemp J. J. Chem. Soc., Chem. Commun. (1977) 125-126
5. Grigg R., and Kemp J. J. Chem. Soc., Chem. Commun. (1978) 109-111
6. Grigg R., and Kemp J. Tetrahedron Lett. 19 (1978) 2823-2826
7. Grigg R., Gunaratne H.Q.N., and Kemp J. J. Chem. Soc., Perkin Trans. 1 (1984) 41-46
8. For a review, see:. Grigg R. Chem. Soc. Rev. 16 (1987) 89-121
9. Grigg R., Donegan G., Gunaratne H.Q.N., Kennedy D.A., Malone J.F., Sridharan V., and Thianpatanagul S. Tetrahedron 45 (1989) 1723-1746
10. Grigg R., Malone J.F., Mongkolaussavaratana T., and Thianpatanagul S. Tetrahedron 45 (1989) 3849-3862
11. Grigg R., and Armstrong P. Tetrahedron 45 (1989) 7581-7586
12. Ardill H., Dorrity M.J.R., Grigg R., Leon-Ling M.-S., Malone J.F., Sridharan V., and Thianpatanagul S. Tetrahedron 46 (1990) 6433-6448
13. Grigg R., Rankovic Z., Thornton-Pett M., and Somasunderam A. Tetrahedron 49 (1993) 8679-8690
14. Grigg R., McMeekin P., and Sridharan V. Tetrahedron 51 (1995) 13331-13346
15. Grigg R., McMeekin P., and Sridharan V. Tetrahedron 51 (1995) 13347-13356 Also see references cited therein
16. For a recent review, see:. Komatsu M., Minakata S., and Oderaotoshi Y. ARKIVOC 7 (2006) 370-389
17. Komatsu M., Ohno M., Tsuno S., and Ohshiro Y. Chem. Lett. 19 (1990) 575-576
18. Ohno M., Komatsu M., Miyata H., and Ohshiro Y. Tetrahedron Lett. 32 (1991) 5813-5816
19. Komatsu M., Okada H., Akaki T., Oderaotoshi Y., and Minakata S. Org. Lett. 4 (2002) 3505-3508
20. Okada H., Akaki T., Oderaotoshi Y., Minakata S., and Komatsu M. Tetrahedron 59 (2003) 197-205
21. Komatsu M., Okada H., Yokoi S., and Minakata S. Tetrahedron Lett. 44 (2003) 1603-1606
22. Komatsu M., Kasano Y., Yonemori J., Oderaotoshi Y., and Minakata S. Chem. Commun. (2006) 526-528 Also see references cited therein
23. A recent review:. Kanemasa S. Synlett (2002) 1371-1387
24. Grigg R., and Gunaratne H.Q.N. J. Chem. Soc., Chem. Commun. (1982) 384-386
25. Amornraksa K., Barr D., Donegan G., Grigg R., Ratananukul P., and Sridharan V. Tetrahedron 45 (1989) 4649-4668
26. Tsuge O., Kanemasa S., and Yoshioka M. J. Org. Chem. 53 (1988) 1384-1391
27. Grigg R., Montgomery J., and Somasunderam A. Tetrahedron 48 (1992) 10431-10442
28. Ayerbe M., Arrieta A., and Cossío F.P. J. Org. Chem. 63 (1998) 1795-1805
29. Vivanco S., Lecea B., Arrieta A., Prieto P., Morao I., Linden A., and Cossío F.P. J. Am. Chem. Soc. 122 (2000) 6078-6092
30. Casas J., Grigg R., Nájera C., and Sansano J.M. Eur. J. Org. Chem. (2001) 1971-1982 Also see references cited therein
31. For reviews, see:. Nájera C., and Sansano J.M. Angew. Chem., Int. Ed. 44 (2005) 6272-6276
32. Husinec S., and Savic V. Tetrahedron: Asymmetry 16 (2005) 2047-2061
33. Gothelf A.S., Gothelf K.V., Hazell R.G., and Jørgensen K.A. Angew. Chem., Int. Ed. 41 (2002) 4236-4238
34. Longmire J.M., Wang B., and Zhang X. J. Am. Chem. Soc. 124 (2002) 13400-13401
35. Chen C., Li X., and Schreiber S.L. J. Am. Chem. Soc. 125 (2003) 10174-10175
36. Oderaotoshi Y., Cheng W., Fujitomi S., Kasano Y., Minakata S., and Komatsu M. Org. Lett. 5 (2003) 5043-5046
37. Gao W., Zhang X., and Raghunath M. Org. Lett. 7 (2005) 4241-4244
38. Alemparte C., Blay G., and Jørgensen K.A. Org. Lett. 7 (2005) 4569-4572
39. Cabrera S., Arrayás R.G., and Carretero J.C. J. Am. Chem. Soc. 127 (2005) 16394-16395 Also see references cited therein
40. Shirai M., Kuwabara H., Matsumoto S., Yamamoto H., Kakehi A., and Noguchi M. Tetrahedron 59 (2003) 4113-4121
41. Noguchi M., Matsumoto S., Shirai M., and Yamamoto H. Tetrahedron 59 (2003) 4123-4133
42. Structures of prolines 8a, 8f, and 8g were confirmed by single-crystal X-ray structure analysis and their crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 604568 for 8a, CCDC 604569 for 8f, and CCDC 604570 for 8g. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
43. Tsuge O., Ueno K., Kanemasa S., and Yorozu K. Bull. Chem. Soc. Jpn. 59 (1986) 1809-1824
44. Fraga-Dubreuil J., Cherouvrier J.R., and Bazureau J.P. Green Chem. 2 (2000) 226-229
45. Peddibhotla S., and Tepe J.J. J. Am. Chem. Soc. 126 (2004) 12776-12777
46. Bowman R.K., and Johnson J.S. J. Org. Chem. 69 (2004) 8537-8540
47. George T., Mehta D.V., and Dabholkar D.A. J. Org. Chem. 36 (1971) 2192-2194
48. Roma G., Di Braccio M., Balbi A., Mazzei M., and Ermili A. J. Heterocycl. Chem. (1987) 329-335
49. Roma G., Ermili A., Braccio M., and Mazzei M. Farmaco Ed. Sci. 37 (1982) 747-758
50. Chem. Abstr. 98 (1983) 53825c