Addition of organocerium reagents to morpholine amides: Synthesis of important pheromone components of Achaea janata

Journal of Organic Chemistry

Volumn 67, Issue 25, 2002, Pages 8938-8942

  Badioli, Michele ^a   Ballini, Roberto ^a   Bartolacci, Massimo ^a   Bosica, Giovanna ^a   Torregiani, Elisabetta ^a   Marcantoni, Enrico ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

STERIC HINDRANCE;

CERIUM COMPOUNDS; ORGANOMETALLICS; SUBSTRATES;

KETONES;

CERIUM; KETONE; LITHIUM DERIVATIVE; MAGNESIUM DERIVATIVE; MORPHOLINE DERIVATIVE; PHEROMONE; AMIDE; ORGANOMETALLIC COMPOUND;

ADDITION REACTION; ARTICLE; POLYMERIZATION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; ANIMAL; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; LEPIDOPTERA; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYSIOLOGY; STRUCTURE ACTIVITY RELATION;

AMIDES; ANIMALS; CATALYSIS; CERIUM; KETONES; LEPIDOPTERA; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; MORPHOLINES; ORGANOMETALLIC COMPOUNDS; PHEROMONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037073825     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0263061     Document Type: Article

References (70)

1. March, J. Advanced Organic Chemistry; 5th ed.; Wiley-Interscience: New York, 2001; pp 1205-1209.
2. (a) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994.
3. (b) Molander, G. A. Chem. Rev. 1992, 92, 29.
4. Imamoto, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Screiber, S. L., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 231-250.
5. (a) Imamoto, T. Pure Appl. Chem. 1990, 62, 747.
6. (b) Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
7. (c) Imamoto, Y.; Takiyama, N.; Nakamura, K. Tetrahedron Lett. 1985, 26, 4763.
8. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904.
9. (a) Panev, S.; Dimitrov, V. Tetrahedron: Asymmetry 2000, 11, 1517.
10. (b) Dimitrov, V.; Kostova, K.; Genov, M. Tetrahedron Lett. 1996, 37, 6787.
11. (c) Bartoli, G.; Marcantoni, E.; Sambri, L.; Tamburini, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2046.
12. (d) Bartoli, G.; Bosco, M.; Sambri, L.; Marcantoni, E. Tetrahedron Lett. 1994, 35, 8651.
13. (e) Bartoli, G.; Sambri, L. Marcantoni, E.; Petrini, M. Tetrahedron Lett. 1994, 35, 8453.
14. (f) Bartoli, G.; Marcantoni, E., Petrini, M. J. Chem. Soc., Chem. Commun. 1993, 1373.
15. (g) Johnson, C. R.; Tait, B. D. J. Org. Chem. 1987, 52, 281.
16. (a) Bartoli, G.; Bosco, M.; Di Martino, E.; Marcantoni, E.; Sambri, L. Eur. J. Org. Chem. 2001, 2901.
17. (b) Dalpozzo, R.; De Nino, A.; Bartoli, G.; Bosco, M.; Sambri, L.; Marcantoni, E. J. Org. Chem. 1998, 63, 3745.
18. (c) Greeves, N.; Pease, J. E. Tetrahedron Lett. 1996, 37, 5821.
19. (d) Bartoli, G.; Marcantoni, E.; Petrini, M.; Sambri, L. Chem. J. Eur. 1996, 2, 913.
20. (e) Denmark S. E.; Weber, T.; Piotrowski, D. W. J. Am. Chem. Soc. 1987, 109, 2224.
21. Kurosu, M.; Kishi, Y. Tetrahedron Lett. 1998, 39, 4793.
22. (a) Bartoli, G.; Bosco, M.; Marcantoni, E.; Massaccesi, M.; Petrini, M.; Sambri, L. J. Org. Chem. 2000, 65, 4563.
23. (b) Ballini, R.; Marcantoni, E.; Perella, S. J. Org. Chem. 1999, 64, 2954.
24. (c) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 120, 2817.
25. (a) Mori, K. Acc. Chem. Res. 2000, 33, 102.
26. (b) Kurosawa, S.; Takenaka, M.; Dunkelblum, E.; Mendel, Z.; Mori, K. ChemBioChem 2001, 1, 56.
27. (a) Ballini, R.; Bosica, G. J. Nat. Prod. 1998, 61, 673.
28. (b) Ballini, R. In Studies in Natural Products Chemistry; Atta-ur Rahman, Ed.; Elsevier: Amsterdam, 1997; Vol. 19, pp 117-184.
29. (c) Ballini, R. Synthesis 1993, 687.
30. (d) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316.
31. (e) Rosini, G.; Ballini, R.; Petrini, M.; Marotta, E. Angew. Chem., Int. Ed. Engl. 1986, 25, 941.
32. (f) Rosini, G.; Marotta, E.; Petrini, M.; Ballini, R. Tetrahedron 1985, 41, 4633.
33. Persoons, C. J.; Vos, J. D.; Yadav, J. S.; Prasad, A. R.; Jyothi, K. N.; Prasuma, A. L. IOBC/WPRS Bull. 1993, 16, 136.
34. (a) Yadav, J. S.; Rajashaker, K.; Venkatram Reddy, K.; Chandrasekhar, S. Synth. Commun. 1998, 28, 4249.
35. (b) Vig, O. P.; Kad, G. L.; Sharma, M. L.; Dogra, V.; Sharma, S.; Huq, M. A.; Sabharwal, A. Collect. Czech. Chem. Commun. 1990, 55, 2252.
36. (c) O'Connor, B.; Just, G. J. Org. Chem. 1987, 52, 1801.
37. (d) Jain, S. C.; Dussord, D. E.; Conner, W. E.; Eisner, T.; Guerrero A.; Meinwald, J. J. Org. Chem. 1983, 48, 2266.
38. Hill, A. S.; Kovalev, B. G.; Nikolaeva, L. N.; Roelofs, W. L. J. Chem. Ecol. 1982, 8, 383.
39. O'Neil, B. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford; 1991; Vol. 1, p 397.
40. (a) Lipshutz, B. H.; Pfeiffer, S. S.; Chrisman, W. Tetrahedron Lett. 1999, 40, 7889.
41. (b) Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
42. Sibi, M. P.; Stassman, C. C.; Schultz, J. A.; Christensen, S. W.; Lu, J.; Marvin, M. Synth. Commun. 1995, 25, 1255, and references cited.
43. (a) Shimizu, T.; Osako, K.; Nakata, T. Tetrahedron Lett. 1997, 38, 2685.
44. (b) Williams, J. M.; Jobson. R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461.
45. Ballini, R.; Marcantoni, E.; Torregiani, E. J. Nat. Prod. 2000, 60, 505.
46. Caglioti, L. Tetrahedron 1966, 22, 636.
47. Tiller, R.; Frey, L. F.; Tschaen, D. M.; Dolling, U.-H. Synlett 1996, 225.
48. (a) Donat, C.; Heitz, A.; Martinez, J.; Fehrentz, J.-A. Tetrahedron Lett. 2000, 41, 37.
49. (b) Sengupta, S.; Mondal, S.; Das, D. Tetrahedron Lett. 1999, 40, 407.
50. (c) Gomtsyan, A. Org. Lett. 1999, 2, 11.
51. (d) Martin, R.; Ronica, P.; Tey, C.; Urpì, F.; Villarasa, J. Synlett 1997, 1414.
52. (e) Tasaka, A.; Tamura, N.; Matsushita, Y.; Kitazaki, T.; Hayashi, R.; Okonogi, K.; Itoh, K. Chem. Pharm. Bull. 1995, 43, 432.
53. (f) Brown, J. D. Tetrahedron: Asymmetry 1992, 3, 1551.
54. Addition of organocerium compounds to Weinreb's amides, see: Brenner-Weiss, G.; Giannis, A.; Sandhoff, K. Tetrahedron 1992, 48, 5855.
55. Morpholine amides of type 12 have been efficiently prepared by reaction of anhydrous morpholine with corresponding acid chloride in the presence of dry pyridine. This reaction works well with linear alkyl and α-branched chain acids and provides a mild and general method for the synthesis of amides. On the other hand, the preparation of amides from acids via the mixed anhydride method does not always provide satisfactory results.
56. 3 prepared by the Imamoto procedure; however, the material was highly efficient without the need of a large excess of Grignard or organolithium reagent.
57. 2O was slower and not as clean.
58. (a) Enders, D.; Schankat, J.; Klatt, M. Synlett 1994, 795.
59. (b) Denmark, S. E.; Edwards, P. J.; Nicaise, O. J. Org. Chem. 1993, 58, 569.
60. Bartoli, G.; Marcantoni, E.; Sambri, L. In Seminars in Organic Synthesis; XXV Summer School "A. Corbella", Gargnano (BS); Italian Chemical Society: Rome, 2000; pp 117-138.
61. Liu, H.-J.; Shia, K.-S.; Shang, X.; Zhu, B.-Y. Tetrahedron 1999, 55, 3803.
62. It is desirable to use the Grignard reagent as the source of transferable alkyl group, which was purchased as solutions in THF and titrated just before use (Bergbreit, D. E.; Pendergross, E. J. Org. Chem. 1981, 46 (6), 219).
63. (a) Hutchins, R. O.; Hutchins, M. C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8, pp 327-349.
64. (b) Yamamura, S.; Nishiyama, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8, pp 307-325.
65. (c) Hudlicky, M. Reductions in Organic Chemistry; Wiley: New York, 1984.
66. (a) Miller, V. P.; Yang, D.; Weigel, T. M.; Han, O.; Liu, H. J. Org. Chem. 1989, 54, 4175.
67. (b) Han, O.; Shih, Y.; Liu, L.; Liu, H. J. Org. Chem. 1988, 53, 2105.
68. Lightner, D. A.; Gawronski, J. K.; Bonman, T. D. J. Am. Chem. Soc. 1980, 102, 1983.
69. Still, W. C.; Khan, M.; Mitra, A. J. Org. Chem. 1978, 43, 2953.
70. Imamoto, T.; Takeda, N. Org. Synth. 1998, 76, 228.