A new strategy for the preparation of an active Mn(0) and its use for radical cyclization reactions

Tetrahedron

Volumn 55, Issue 7, 1999, Pages 1893-1904

  Tang, Jun ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MANGANESE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY;

EID: 0033548015     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01205-8     Document Type: Article

References (59)

1. (a) Normant, K. F.; Cahiez, G. In Modern Synthetic Methods; Schefford, R., Ed.; Salle and Savenlander: Frankfurt, 1983, vol. 3.
2. (b) Cahiez, G. Butylmanganese Chloride and Related Reagents in Encyclopedia of Reagents for Organic Synthesis; Paquette, L., Ed.; Wiley: Chichester, 1995.
3. (c) Cahiez, G. Manganese(II) Chloride in Encyclopedia of Reagents for Organic Synthesis; Paquette, L., Ed.; Wiley: Chichester, 1995.
4. (d) Cahiez, G. and Marquais, S. Pure & Appl. Chem. 1996, 68, 53.
5. (e) Rieke, R. D.; Kim, S-H.; Wu, X. M. J. Org. Chem. 1997, 62, 6921.
6. (f) Kang, S-K.; Kim, W-Y.; Lee, Y-T.; Kim, J-C. Tetrahedron Lett. 1998, 39, 2131.
7. (g) Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Tetrahedron 1997, 53, 5061.
8. (a) Snider, B. B. Chem. Rev. 1996, 96, 339.
9. (b) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519.
10. (a) Takai, K.; Ueda. T.; Ikeda, N.; Moriwake, T. J. Org. Chem. 1996, 61, 7990.
11. (b) Takai, K.; Ueda. T.; Kaihara, H; Sunami, Y.; Moriwake, T. J. Org. Chem. 1996, 61, 8728.
12. (a) Nakao, J.; Inoue, R.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1997, 62, 6050.
13. (b) Nakao, J.; Inoue, R.; Shinokubo, H.; Oshima, K. Bull. Chem. Soc. Jpn. 1997, 70, 2039.
14. For leading references, see: (a) Hart, D. J. Science 1984, 223, 883.
15. (b) Curran, D. P. Synthesis 1988, 417, 489.
16. (c) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic: New York, 1992.
17. (d) Melikyan, Gagik G. Org. React. 1997, 49, 427.
18. (a) Sloan, C. P.; Cuevas, J. C.; Quesnelle, C.; Snieckus, V. Tetrahedron Lett. 1988, 29, 4685.
19. (b) Wolff, S.; Hoffmann, H. M. R. Synthesis 1988, 760.
20. (c) Boger, D. L.; Palanki, M. S. S. J. Am. Chem. Soc. 1992, 114 , 9318.
21. (d) Rao, A. V. R.; Gurjar, M. K.; Bose, D. S.; Devi, R. R. J. Org. Chem. 1991, 56, 1320.
22. (e) Boger, D. L.; Yun, W.; Teegarden, B. R. J. Org. Chem., 1992, 57, 2873.
23. (f) Clive, D. L. J.; Etkin, N.; Joseph, T.; Lown, J. W. J. Org. Chem. 1993, 58, 2442.
24. (g) Boisvert, G.; Giasson, R. Tetrahedron Lett. 1992, 33, 6587.
25. (h) Rai. R.; Collum, D. B. Tetrahedron Lett. 1994, 35, 6221.
26. (i) Itoh, T.; Ohara, H.; Emoto, S. Tetrahedron Lett. 1995, 36, 3531.
27. Palladium-catalyzed cyclization: (a) Larock R. C.; Stinn, D. E. Tetrahedron Lett. 1988, 29, 4687.
28. (b) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291.
29. (c) Larock, R. C.; Stinn, D. E. Tetrahedron Lett. 1989, 30, 2767.
30. (d) Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113.
31. (e) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1988, 27, 2225. Nickel:
32. (f) Mori, M.; Kudo, S.; Ban, Y. J. Chem. Soc., Perkin Trans. I 1978, 771.
33. (g) Olivero, S.; Clinet, J. C.; Dunach, E. Tetrahedron Lett. 1995, 36, 4429. Cobalt:
34. (h) Pattenden, G. Chem. Soc. Rev. 1988, 7, 361. Zn-Mn:
35. (i) Riguet, E.; Klement, I; Reddy, C. K.; Cahiez, G.; Knochel, P. Tetrahedron Lett. 1996, 37, 5865. Zn-Ni:
36. (j) Vaupel, A.; Knochel, P. J. Org. Chem. 1996, 61, 5743.
37. Curran, D. P.; Totleben, M. J. J. Am. Chem. Soc. 1992, 14, 6050.
38. Hojo, M.; Yoshizawa, J.; Funahashi, Y.; Okada, R.; Nakayama, S.; Tateiwa, J.; Hosomi, A. Heterocycles, in press.
39. A part of this paper was publicated in a communication: Tang, J.; Shinokubo, H.; Oshima, K. Synlett 1998, 1075.
40. Metal granules 1-3 mm purchased from Mitsuwa's pure chemicals.
41. The blank test without manganese species was performed as follows: The fully activated magnesium turnings were stirred in THF for 24 h, and the supernatant (5 mL) was added to the flask containing 1b (X=I, 1.0 mmol) in THF (2 mL). No reaction took place after 24 h from which 90% of the starting material was recovered unchanged.
42. Cahiez, G.; Alami, Tetrahedron 1989, 45, 4163.
43. 8K: Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009.
44. 8K: Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009.
45. 8K: Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009.
46. Treatment of b (X=I) with commercially available manganese powder (Kanto Chemical Co. Inc) at °C for h resulted in a complete recovery of the starting material. Several procedure for an activation of Mn metal has been reported: (a) Hiyama. T.; Sawahata, M.; Obayashi, M. Chem. Lett. 1983, 1237.
47. (b) Cahiez, G.; Chavant, P. Y. Tetrahedron Lett. 1989, 30, 7373.
48. (c) Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett. 1996, 37, 7049.
49. Stork, G.; Sher, P. M.; Chen, H.-L. J. Am. Chem. Soc. 1986, 108, 6384.
50. Shimizu, I.; Sugiura, T.; Tsuji, J. J. Org. Chem. 1985, 50, 537.
51. -1). For the detail please see: Newcomb, M.; Curran, D. P. Acc. Chem. Res. 1988, 21, 206. and references therein.
52. Stork, G.; Jr. Mook, R. J. Am. Chem. Soc. 1983, 105, 3720.
53. 3SnH afforded 2i in 85% yield, however the workup and purification of the products were troublesome.
54. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
55. 1H NMR spectra. Characterization of the products is based on the corresponding lactones after Jones oxidation.
56. Morikawa, T.; Nishiwaki, N.; Iitake, Y.; Kobayashi, Y. Tetrahedron Lett. 1987, 28, 671.
57. 5-exo mode cyclization of 11 to form trans-fused 2-oxabicyclo[3.3.0]octane might be unfavorable. 25. The presence of the manganese enolate could also be supported by the following reaction. (Formula presented)
58. If the magnesium turnings were not fully activiated, this reductive reaction shoud not be initiated. In such case, a small amount of 1,2-dibromoethane (ca. 3 mmol) was added to the above suspension and the reductive reaction should take place at once
59. The content of manganese in this supernatant could be simplely determined by acid-base titration method and the details are as follows: supernatant (2 mL) was transfered with a syringe to a flask under argon atmosphere, and quenched it with standard hydrochloric acid (0.100 mmol/mL, 10 mL) at 0 °C. The excess hydrochloric acid was titrated by a standard sodium hydroxide (0.100 mmol/mL) with phenol phthalein as an indicator. Upon this method, the factor is about 0.29 mmol Mn(0)/mL.