Excellent chiral introduction by diene iron-tricarbonyl moiety. III: Asymmetric synthesis of hydroxyethylidene dipeptide isostere using a diastereoselective 1,2-nucleophilic addition of organocerium reagents into a 1-azatriene Fe(CO)3 complex

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 5, 1996, Pages 948-955

  Takemoto, Yoshiji ^a   Takeuchi, Jun ^a   Matsui, Eiki ^a   Iwata, Chuzo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

1,2 nucleophilic addition; 1,4 functionalization; 1 azatriene iron tricarbonyl complex; Hydroxyethylidene dipeptide isostere; Iodocyclocarbamation; Organocerium reagent

Indexed keywords

ACTINOBOLIN; CARBONYL IRON; CERIUM; CLAVIPECTIN B; HYDROXYETHYLIDENE DIPEPTIDE ISOSTERE; IRON TRICARBONYL; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0029974953     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.948     Document Type: Article

References (57)

1. Takemoto Y., Takeuchi J., Mono K., Nakamoto T., Iwata C., Chem Pharm. Bull., 44, 940-947 (1996).
2. For reviews on organometallic additions to imines and their derivatives, see; a) Volkmann R. A., "Comprehensive Organic Synthesis," Vol. 1, ed. by Trost B. M., Fleming I. E., Pergamon Press, Oxford, 1991, pp. 355-396; b) Kleinman E., "Comprehensive Organic Synthesis," Vol. 2, ed. by Trost B. M., Fleming I. E., Pergamon Press, Oxford, 1991, pp. 893-952;
3. For reviews on organometallic additions to imines and their derivatives, see; a) Volkmann R. A., "Comprehensive Organic Synthesis," Vol. 1, ed. by Trost B. M., Fleming I. E., Pergamon Press, Oxford, 1991, pp. 355-396; b) Kleinman E., "Comprehensive Organic Synthesis," Vol. 2, ed. by Trost B. M., Fleming I. E., Pergamon Press, Oxford, 1991, pp. 893-952;
4. c) Recently, the asymmetric control in the addition reaction to imines using an external chiral ligand has been reported; Inoue I., Shindo M., Koga K., Tomioka K., Tetrahedron, 50, 4429-4438 (1994); Denmark S. E., Nakajima N., Nicaise O. J.-C., J. Am. Chem. Soc., 116, 8797-8798 (1994).
5. c) Recently, the asymmetric control in the addition reaction to imines using an external chiral ligand has been reported; Inoue I., Shindo M., Koga K., Tomioka K., Tetrahedron, 50, 4429-4438 (1994); Denmark S. E., Nakajima N., Nicaise O. J.-C., J. Am. Chem. Soc., 116, 8797-8798 (1994).
6. a) Yamamoto Y., Komatsu T., Maruyama K., J. Am. Chem. Soc., 106, 5031-5033 (1984);
7. b) Yamamoto Y., Nishii S., Maruyama K., Komatsu T., Ito W., ibid., 108, 7778-7786 (1986);
8. c) Yamamoto Y., Ito W., Tetrahedron, 44, 5415-5423 (1988);
9. d) Boga C., Savoia D., Umani-Ronchi A., Tetrahedron: Asymmetry, 1, 291-294 (1990);
10. e) Bocoum A., Boga C., Savoia D., Umani-Ronchi A., Tetrahedron Lett., 32, 1367-1370 (1991);
11. f) Beuchet P., L-Marrec N., Mosset P., ibid., 33, 5959-5960 (1992);
12. g) Hallett D. J., Thomas E. J., J. Chem. Soc., Chem. Commun., 1995, 657-658.
13. a) Takahashi H., Suzuki Y., Inagaki H., Chem. Pharm. Bull., 30, 3160-3166 (1982);
14. b) Takahashi H., Suzuki Y., Hori T., ibid., 31, 2183- 2191 (1983);
15. c) Takahashi H., Chida Y., Suzuki T., Yanaura S., Suzuki Y., Masuda C., ibid., 31, 1659-1665 (1983);
16. d) Suzuki Y., Takahashi H., ibid., 31, 2895-2898 (1983);
17. e) Tanaka H., Inoue K., Pokorski U., Taniguchi M., Torii S., Tetrahedron Lett., 31, 3023-3026 (1990);
18. f) Higashiyama K., Inoue H., Takahashi H., ibid., 33, 235-238 (1992);
19. g) Giammaruco M., Taddei M., Ulivi P., ibid., 34, 3635-3638 (1993);
20. h) Bhuyan P-J., Prajapati D., Sandhu J-S., ibid., 34, 7975-7976 (1993);
21. i) Basile T., Bocoum A., Savoia D., Umani-Ronchi A., J. Org. Chem., 59, 7766-7773 (1994).
22. a) Ukaji Y., Watai T., Sumi T., Fujisawa T., Chem Lett., 1991, 1555- 1558;
23. b) Dembele Y-A., Belaud C., Villieras J., Tetrahedron: Asymmetry 3, 511-514 (1992);
24. c) Higashiyama K., Fujikura H., Takahashi H., Chem. Pharm. Bull., 43, 722-728 (1995).
25. a) Franck-Neumann M., "Organometallics in Organic Synthesis," ed. by de. Meijere A., Dieck H. T., Springer-Verlag, Berlin, 1987. pp. 247-264;
26. b) Gree R., Synthesis, 1989, 341-355;
27. c) Pearson A. J., "Iron Compounds in Organic Synthesis," Academic Press, London, 1994, pp. 67-96;
28. d) Tao C., Donaldson W. A., J. Org. Chem., 58, 2134-2143 (1993);
29. e) Roush W. R., Wada C. K., J. Am. Chem. Soc., 116, 2151-2152 (1994);
30. f) Takemoto Y., Ueda S., Takeuchi J., Nakamoto T., Iwata C., Tetrahedron Lett., 35, 8821-8824 (1994);
31. g) Takemoto Y., Ueda S., Takeuchi J., Nakamoto T., Iwata C., Ohishi H., Sakaguchi K., Kusunoki M., Chem. Pharm. Bull., 43, 559-563 (1995);
32. h) Takemoto Y., Yoshikawa N., Iwata C., J. Chem. Soc., Chem. Commun., 1995, 631-632.
33. a) Franck-Neumann M., Chemla P., Martina D., Synlett, 1990, 641-642;
34. b) Takemoto Y., Takeuchi J., Iwata C., Tetrahedron Lett., 34, 6067-6068 (1993).
35. Teniou A., Toupet L., Gree R., Synlett, 1991, 195-197.
36. Raub M. F., Cardellina J. H. II., Choudhary M. I., Ni C-Z., Clardy J., Alley M. C., J. Am. Chem. Soc., 113, 3178-3180 (1991).
37. Oppolzer W., "Comprehensive Organic Synthesis," Vol. 5, ed. by Trost B. M., Fleming I. E., Pergamon Press, Oxford, 1991, pp. 315-400.
38. Kozikowski A. P., Nieduzak T. R., Konoike T., Springer J. P., J. Am. Chem. Soc., 109, 5167-5175 (1987).
39. a) Carson K. G., Ganem B., Radin N. S., Abe A., Shayman J. A., Tetrahedron Lett., 35, 2659-2662 (1994);
40. b) Jefford C. W., McNulty J., Lu Z-H., J. Chem. Soc., Chem. Commun., 1995, 123-124.
41. a) Hanson G. J., Lindberg T., J. Org. Chem., 50, 5399-5401 (1985);
42. b) Kaltenbronn J. S., Hudspeth J. P., Lunney E. A., Michniewicz B. M., Nicolaides E. D., Repine J. T., Roark W. H., Stier M. A., Tinney F. J., Woo P. K. W., Essenburg A. D., J. Med. Chem., 33, 838-845 (1990).
43. A part of this work has been published in a preliminary communication; Takemoto Y., Takeuchi J., Iwata C., Tetrahedron Lett., 34, 6069-6072 (1993).
44. a) Whitlock H. W., Jr., Reich C., Woessner W. D., J. Am. Chem. Soc., 93, 2483-2492 (1971);
45. b) Franck-Neumann M., Martina D., Heitz M. P., Tetrahedron Lett., 23, 3493-3496 (1982).
46. Wada M., Sakurai Y., Akiba K., Nippon Kagaku Kaishi, 1985, 295-302.
47. a) Imamoto T., Kusumoto T., Tawarayama Y., Sugiura Y., Mita T., Hatanaka Y., Yokoyama M., J. Org. Chem., 49, 3904-3912 (1984);
48. b) Imamoto T., Takiyama N., Nakamura K., Hatajima T., Kamiya Y., J. Am. Chem. Soc., 111, 4392-4398 (1989).
49. a) Clinton N. A., Lillya C. P., J. Am. Chem. Soc., 92, 3058-3064 (1970);
50. b) Recently, Y. Troin et al. assigned the stereochemistry of secondary amine complexes by their Rf values according to Lillya's method; Ripoche I., Gelas J., Gree D., Gree R., Troin Y., Tetrahedron Lett., 36, 6675-6678 (1995).
51. a) Shue Y-K., Carrera G. M., Tufano M. D., Nadzan A. M., J. Org. Chem., 56, 2107-2111 (1991); and references cited therein;
52. b) Ibuka T., Habashita H., Otaka A., Fujii N., ibid., 56, 4370-4382 (1991);
53. c) McKinney J. A., Eppley D. F., Keenan R. M., Tetrahedron Lett., 35, 5985-5988 (1994).
54. Takemoto Y., Takeuchi J., Matsui E., Iwata C., Synlett, 1995, 737-738.
55. Parker K. A., O'Fee R., J. Am. Chem. Soc., 105, 654-655 (1983).
56. Birch A. J., Liepa A. J., Stephenson G. R., Tetrahedron Lett., 1979, 3565-3568 (1979).
57. a) See references 3d, 5a); b) Matsumoto T., Kobayashi Y., Takemoto Y., Ito Y., Kamijo T., Harada H., Terashima S., Tetrahedron Lett., 31, 4175-4176 (1990).