Reaction of 2,3-allenoates with TsNBr2 in the presence of base: A facile highly stereoselective synthesis of (1E,2E)-3-bromo-4-oxo-N′- tosyl-2-alkenoxylimidic acid ethyl esters

Journal of Organic Chemistry

Volumn 72, Issue 10, 2007, Pages 3961-3964

  Shen, Ruwei ^a   Huang, Xian ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2,3-ALLENOATES; ELECTROPHILES; ETHYL ESTERS; TSNBR2;

BROMINE COMPOUNDS; ORGANIC ACIDS; REACTION KINETICS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

ESTERS;

3 BROMO 4 OXO N' TOSYL 2 ALKENOXYLIMIDIC ACID ETHYL ESTER; ALLENE DERIVATIVE; ESTER DERIVATIVE; N,N DIBROMO 4 TOLUENSULFONAMIDE; POTASSIUM CARBONATE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 34248598925     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070239z     Document Type: Article

References (68)

1. (a) Patai, S. The Chemistry of Ketenes, Allenes, and Related Compounds; John Wiley & Sons: New York, 1980; Part 1.
2. (b) Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley & Sons: New York, 1984.
3. (c) Landor, S. R. The Chemistry of Allenes; Academic Press: New York, 1982; Vols. 1-3.
4. (d) Krause, N.; Hashmi, A. S. K. Modern Allene Chemistry; Wiley-VCH: Weinheim, Germany, 2004; Vols. 1-2.
5. (a) Smadja, W. Chem. Rev. 1983, 83, 263.
6. (b) Marshall, J. A. Chem. Rev. 1996, 96, 31.
7. (c) Yamamoto, Y.; Radhakrishnan, U. Chem. Soc. Rev. 1999, 28, 199.
8. (d) Hashimi, A. S. K. Angew. Chem., Int. Ed. 2000, 39, 3590.
9. (e) Ma, S. Acc. Chem. Res. 2003, 36, 701.
10. (f) Ma, S. Chem. Rev. 2005, 105, 2829.
11. (g) Reissing, H. U.; Schade, W.; Amombo, M. O.; Pulz, R.; Hausherr, A. Pure Appl. Chem. 2002, 175.
12. For recent examples, see: (a) Ohno, H.; Miyamura, K.; Mizutani, T.; Kadoh, Y.; Takeoka, Y.; Hamaguchi, H.; Tanaka, T. Chem. - Eur. J. 2005, 11, 3728.
13. (b) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. Angew. Chem., Int. Ed. 2006, 45, 2459.
14. (c) Brummond, K. M.; Gao, D. Org. Lett. 2003, 5, 3491.
15. (d) Mukai, C.; Takahashi, Y. Y. Org. Lett. 2005, 7, 5793.
16. (e) Ma, S.; Jiao, N.; Zheng, Z.; Ma, Z.; Lu, Z.; Ye, L.; Deng, Y.; Chen, G. Org. Lett. 2004, 6, 2193.
17. (f) Hamaguchi, H. S.; Kosaka; Ohno, H.; Tanaka, T. Angew. Chem., Int. Ed. 2005, 44, 1513.
18. (g) Zhu, G.; Zhang, Z. Org. Lett. 2004, 6, 4041.
19. (h) Inagaki, F.; Mukai, C. Org. Lett. 2006, 8, 1217.
20. (i) Kuroda, N.; Takahashi, Y.; Yoshinaga, K.; Mukai, C. Org. Lett. 2006, 8, 1843.
21. (j) Ohno, H.; Takeoka, Y.; Miyamura, K.; Kadoh, Y.; Tanaka, T. Org. Lett. 2003, 5, 4763.
22. (k) Feldman, K. S.; Iyer, M. R. J. Am. Chem. Soc. 2005, 127, 4590.
23. (l) Ma, S.; Gu, Z. J. Am. Chem. Soc. 2005, 127, 6182.
24. (m) Parthasarathy, K.; Jeganmohan, M.; Cheng, C.-H. J. Am. Chem. Soc. 2006, 128, 621.
25. (a) Ma, S.; Ren, H.; Wei, Q. J. Am. Chem. Soc. 2003, 125, 4817.
26. (b) Ma, S.; Wei, Q. Eur. J. Org. Chem. 2000, 1, 1939.
27. (c) Ma, S.; Wei, Q.; Wang, H. Org. Lett. 2000, 2, 3893.
28. (d) Ma, S.; Li, L. Synlett 2001, 1, 1206 and refs therein.
29. For recent examples, see: (a) Zhu, X. F.; Schaffner, A. P.; Li, R. C.; Kwon, O. Org. Lett. 2005, 7, 2977.
30. (b) Dieter, R. K.; Lu, K.; Velu, S. E. J. Org. Chem. 2000, 65, 8715.
31. (c) Chakravarty, M.; Kumara Swamy, K. C. J. Org. Chem. 2006, 71, 9128.
32. (d) Hopkins, C. D.; Guan, L.; Malinakova, H. C. J. Org. Chem. 2005, 70, 6848.
33. (e) Lambert, T. H.; Macmillan, D. W. J. Am. Chem. Soc. 2002, 124, 13646.
34. (f) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677.
35. (g) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
36. (h) Yoshino, T.; Ng, F.; Danishefsky, S. J. J. Am. Chem. Soc. 2006, 128, 14185.
37. (i) Jung, M. E.; Murakami, M. Org. Lett. 2006, 8, 5857.
38. Chen, G.; Fu, C.; Ma, S. J. Org. Chem. 2006, 71, 9877.
39. (a) Hanessian, S. The Total Synthesis of Natural Products: The Chiron Approach; Pergamon Press: New York, 1983; Chapter 9.
40. (b) de March, P.; Font, J.; Gracia, A.; Zheng, Q. J. Org. Chem. 1995, 60, 1814.
41. (c) Fu, C.; Ma, S. Eur. J. Org. Chem. 2005, 3942.
42. (d) Chen, G.; Fu, C.; Ma, S. Tetrahedron 2006, 62, 4444.
43. (e) Ma, S.; Wu, S. Tetrahedron Lett. 2001, 42, 4075.
44. (f) Marshall, J. A.; Bartley, G. S.; Wallace, E. M. J. Org. Chem. 1996, 61, 5729.
45. 2, see: (a) Nair, C. G. R.; Indrasen, P. Talanta 1976, 23, 239.
46. (b) Tajbakhsh, M.; Khazaei, A.; Mahalli, M. S.; Vaghi, R. G. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 1159-1163.
47. (c) Saburo, A.; Kenzo, O. J. Am. Chem. Soc. 1954, 76, 693.
48. (a) Kharasch, M. S.; Priestley, H. N. J. Am. Chem. Soc. 1939, 61, 3425.
49. (b) Terauchi, H.; Kowata, K.; Minematsu, T.; Takemura, S. Chem. Pharm. Bull. 1977, 25, 556.
50. (c) Hegedus, L. S.; McKearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444.
51. (d) Revesz, L.; Blum, E.; Wicki, R. Tetrahedron Lett. 2005, 46, 5577.
52. (e) Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 9526.
53. Phukan, P.; Chakraborty, P.; Kataki, D. J. Org. Chem. 2006, 71, 7533.
54. (a) Neilson, D. G. In The Chemistry of Amdines and Imidates; Patai, S., Ed.; John Wiley & Sons: London, UK, 1975; Chapter 8.
55. (b) Kantlehner, W. Synthesis of Iminium Salts, Orthoesters and Related Compounds. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 2. pp 485-599.
56. (c) Baindur, N.; Neumeyer, J. L.; Niznik, H. B.; Bozowej, N. H.; Jarvie, K. R.; Seeman, P.; Garlick, R. K.; Miller, J. J., Jr. J. Med. Chem. 1988, 31, 2069-2071.
57. (d) Yoo, E. J.; Bae, I.; Cho, S. H.; Han, H.; Chang, S. Org. Lett. 2006, 8, 1347.
58. (e) Nikolaev, V.; Hennig, L.; Sieler, J.; Rodina, L.; Schulze, Ba.; Nikolaev, V. Org. Biomol. Chem. 2005, 3, 4108.
59. (a) Jacobs, T. L.; Macomber, R.; Zunker, D. J. Am. Chem. Soc. 1967, 89, 7001.
60. (b) Macomber, R. S. J. Am. Chem. Soc. 1977, 99, 3072.
61. (c) Bollinger, J. M.; Brinich, J. M.; Olah, G. A. J. Am. Chem. Soc. 1970, 92, 4025.
62. (a) Macomber, R. S.; Krudy, G. A.; Seff, K.; Rendon-Diazmiron, L. E. J. Org. Chem. 1983, 48, 1425.
63. (b) Xu, Q.; Huang, X.; Yuan, J. J. Org. Chem. 2005, 70, 6948.
64. (c) Christov, V. C.; Prodanov, B. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 243.
65. (a) Konig, G. M.; Wright, A. D. Planta Med. 1996, 62, 193.
66. (b) Pietra, F. Nat. Prod. Rep. 1997, 14, 453.
67. (c) Osterhage, C.; Kaminsky, R.; Koenig, G. M.; Wright, A. D. J. Org. Chem. 2000, 65, 6412.
68. (d) Yamaguchi, J.; Kakeya, H.; Uno, T.; Shoji, M.; Osada, H.; Hayashi, Y. Angew. Chem., Int. Ed. 2005, 40, 3110.