Sequential addition reactions of lithium aeetylides and grignard reagents to selenoiminium salts leading to 2-propynyl tertiary amines bearing a tetrasubstituted carbon center

Bulletin of the Chemical Society of Japan

Volumn 80, Issue 11, 2007, Pages 2220-2225

  Murai, Toshiaki ^a   Nogawa, Sho ^a   Mutoh, Yuichiro ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COMPONENT COUPLINGS; DIASTEREO SELECTIVITIES; ELEMENTAL SELENIUMS; GOOD YIELDS; GRIGNARD REAGENTS; HIGH EFFICIENCIES; IN-SITU; PHENYLACETYLENE; SECONDARY AMINES; SEQUENTIAL ADDITIONS; TERMINAL ACETYLENES; TERTIARY AMINES; TETRASUBSTITUTED CARBONS; TRIMETHYLSILYL;

ACETYLENE; ADDITION REACTIONS; AMINATION; AROMATIC HYDROCARBONS; BEARINGS (STRUCTURAL); BROMINE COMPOUNDS; CHEMICAL REACTIONS; LIGHTING; LITHIUM; OPTICAL SENSORS; ORGANIC COMPOUNDS; SALTS; SELENIUM; SYNTHESIS (CHEMICAL);

AMINES;

EID: 50549089971     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.80.2220     Document Type: Article

References (82)

1. For recent reviews of multiple-component coupling reactions:
2. a) H. Nemoto, J. Synth. Org. Chem. Jpn. 2004, 62, 347.
3. b) Y. Ishii, S. Sakaguchi, Bull. Chem. Sac. Jpn. 2004, 77, 909.
4. c) S. Kamijo, Y. Yamamoto, J. Synth. Org. Chem. Jpn. 2004, 62, 682.
5. d) C. Wei, Z. Li, C.-J. Li, Synlett 2004, 1472.
6. e) K. Yamada, Y. Yamamoto, K. Tomioka, J. Synth. Org. Chem. Jpn. 2004, 62, 1158.
7. f) G. Balme, Angew. Chem., Int. Ed. 2004, 43, 6238.
8. g) M. Kimura, J. Synth. Org. Chem. Jpn. 2006, 64, 130.
9. h) G. Guillena, D. J. Ramón, M. Yus, Tetrahedron: Asymmetry 2007, 18, 693.
10. i) M. Vrettou, A. A. Gray, A. R. E. Brewer, A. G. M. Barrett, Tetrahedron 2007, 63, 1487.
11. For recent examples:
12. a) C. Wei, C.-J. Li, J. Am. Chem. Soc. 2003, 125, 9584.
13. b) N. E. Leadbeater, H. M. Torenius, H. Tye, Mol. Diversity 2003, 7, 135.
14. c) N. Gommermann, C. Koradin, K. Polborn, P. Knochel, Angew. Chem., Int. Ed. 2003, 42, 5763.
15. d) L. Shi, Y.-Q. Tu, M. Wang, F.-M. Zhang, C.-A. Fan, Org. Lett. 2004, 6, 1001.
16. e) Z. Li, C. Wei, L. Chen, R. S. Varma, C.J. Li, Tetrahedron Lett. 2004, 45, 2443.
17. f) J. S. Yadav, B. V. S. Reddy, V. Naveenkumar, R. S. Rao, K. Nagaiah, New J. Chem. 2004, 28, 335.
18. g) B. M. Choudary, C. Sridhar, M. L. Kantam, B. Sreedhar, Tetrahedron Lett. 2004, 45, 7319.
19. h) T. F. Knopfel, P. Aschwanden, T. Ichikawa, T. Watanabe, E. M. Carreira, Angew. Chem., Int. Ed. 2004, 43, 5971.
20. i) S. B. Park, H. Alper, Chem. Commun. 2005, 1315.
21. j) B. M. Trost, M. T. Rudd, J. Am. Chem. Soc. 2005, 127, 4763.
22. k) Q. Xu, E. Rozners, Org. Lett. 2005, 7, 2821.
23. Y. Yamamoto, H. Hayashi, T. Saigoku, H. Nishiyama, J. Am. Chem. Soc. 2005, 127, 10804.
24. m) N. Gommermann, P. Knochel, Chem. Commun. 2005, 4175.
25. n) B. Sreedhar, P. S. Reddy, B. V. Prakash, A. Ravindra, Tetrahedron Lett. 2005, 46, 7019.
26. o) M. L. Kantam, B. V. Prakash, C. R. V. Reddy, B. Sreedhar, Synlett 2005, 2329.
27. p) X. Guinchard, Y. Vallee, J.-N. Denis, Org. Lett. 2005, 7, 5147.
28. q) N. Gommermann, P. Knochel, Synlett 2005, 2799.
29. r) L. Zani, S. Alesi, P. G. Gozzi, C. Bolm, J. Org. Chem. 2006, 71, 1558.
30. s) A. Bisai, V. K. Singh, Org. Lett. 2006, 8, 2405.
31. t) N. Gommermann, P. Knochel, Chem. Eur. J. 2006, 12, 4380.
32. u) K. Mohan Reddy, N. Seshu Babu, I. Suryanarayana, P. S. Sai Prasad, N. Lingaiah, Tetrahedron Lett. 2006, 47, 7563.
33. v) N. Gommermann, P. Knochel, Org. Synth. 2007, 84, 1.
34. w) P. Li, L. Wang, Tetrahedron 2007, 63, 5455.
35. a) C. W. Kruse, R. F. Kleinschmidt, J. Am. Chem. Soc. 1961, 83, 216.
36. b) G. F. Hennion, A. C. Perrino, J. Org. Chem. 1961, 26, 1073.
37. c) N. R. Easton, D. R. Cassidy, R. D. Dillard, J. Org. Chem, 1963, 28, 448.
38. d) G. F. Hennion, C. V. DiGiovanna, J. Org. Chem. 1965, 30, 3696.
39. e) H. Frey, G. Kaupp, Synthesis 1990, 931.
40. f) R. Geri, C. Polizzi, L. Lardicci, A. M. Caporusso, Gazz. Chim. Ital. 1994, 124, 241.
41. g) R. Nussbaumer, I. Leitner, K. Mraz, A. Stuetz, J. Med. Chem. 1995, 38, 1831.
42. h) I. A. Poplavskaya, T. B. Dembitskaya, Zh. Org. Khim. 1995, 31, 665.
43. i) D. Semeril, J. Le Norte, C. Bruneau, P. H. Dixneuf, A. F. Kolomiets, S. N. Osipov, New J. Chem. 2001, 25, 16.
44. j) M. Z. Ovakimyan, S. K. Barsegyan, M. G. Indzhikyan, Russ. J. Chem. 2002, 72, 1938.
45. k) J. W. Lane, R. L. Halcomb, Org. Lett. 2003, 5, 4017.
46. H. Fukumoto, K. Takahashi, J. Ishihara, S. Hatakeyama, Angew. Chem., Int. Ed. 2006, 45, 2731.
47. m) A. Arcadi, F. Marinelli, L. Rossi, M. Verdecchia, Synthesis 2006, 2019.
48. a) T. Murai, Y. Mutoh, Y. Ohta, M. Murakami, J. Am. Chem. Soc. 2004, 126, 5968.
49. b) T. Murai, R. Toshio, Y. Mutoh, Tetrahedron 2006, 62, 6312.
50. For recent reviews:
51. a) A. J. Moore, in Comprehensive Organic Functional Group Transformations II, ed. by A. R. Katritzky, R. J. K. Taylor, Elsevier Ltd., Oxford, 2005, Vol. 5, p. 519.
52. b) C. Flynn, L. Haughton, in Comprehensive Organic Functional Group Transformations II, ed. by A. R. Katritzky, R. J. K. Taylor, Elsevier Ltd., Oxford, 2005, Vol. 5, p. 571.
53. c) T. Murai, in Topics in Current Chemistry, ed. by S. Kato, Springer GmbH, Heidelberg, 2005, p. 247.
54. d) M. Koketsu, H. Ishihara, Curr, Org, Synth. 2007, 4, 15.
55. e) M. Koketsu, H. Ishihara, in Handbook of Chalcogen Chemistry: New Perspectives in Sulfur, Selenium, Tellurium, ed. by F. A. Devillanova, Royal Society of Chemistry, Cambridge, 2007, pp. 145-194.
56. a) J. Bethke, K. Karaghiosoff, L. A. Wessjohan, Tetrahedron Lett. 2003, 44, 6911.
57. b) V. Saravanan, C. Mukherjee, S. Das, S. Chandrasekaran, Tetrahedron Lett. 2004, 45, 681.
58. c) G. Hua, Y. Li, A. M. Z. Alexandra, J. D. Woollins, Org. Lett. 2006, 8, 5251.
59. a) T. Murai, H. Aso, Y. Tatematsu, Y. Itoh, H. Niwa, S. Kato, J. Org. Chem. 2003, 68, 8514.
60. b) T. Murai, H. Niwa, T. Kimura, F. Shibahara, Chem. Lett. 2004, 33, 508.
61. c) T. Murai, Y. Ohta, Y. Mutoh, Tetrahedron Lett. 2005, 46, 3637.
62. d) T. Murai, H. Sano, H. Kawai, H. Aso, F. Shibahara, J. Org. Chem. 2005, 70, 8148.
63. e) T. Murai, Y. Mutoh, K. Fukushima, Lett. Org. Chem. 2006, 3, 409.
64. f) F. Shibahara, A. Kitagawa, E. Yamaguchi, T. Murai, Org. Lett. 2006, 8, 5621.
65. g) T. Murai, F. Asai, J. Am. Chem. Soc. 2007, 129, 780.
66. h) F. Shibahara, A. Suenami, A. Yoshida, T. Murai, Chem. Commun. 2007, 2354.
67. a) T. Murai, H. Aso, S. Kato, Org. Lett. 2002, 4, 1407.
68. b) T. Murai, M. Ishizuka, A. Suzuki, S. Kato, Tetrahedron Lett. 2003, 44, 1343.
69. c) Y. Mutoh, T. Murai, Org. Lett. 2003, 5, 1361.
70. d) T. Murai, A. Fujishima, C. Iwamoto, S. Kato, J. Org. Chem. 2003, 68, 8514.
71. e) Y. Mutoh, T. Murai, Organometallics 2004, 23, 3907.
72. a) Y. Mutoh, T. Murai, S. Yamago, J. Am. Chem. Soc. 2004, 126, 16696.
73. b) Y. Mutoh, T. Murai, S. Yamago, J. Organomet. Chem. 2007, 692, 129.
74. T. Murai, T. Ezaka, S. Kato, Bull. Chem. Soc. Jpn. 1998, 71, 1193.
75. M. Koketsu, Y. Okayama, H. Aoki, H. Ishihara, Fteteroat. Chem. 2002, 13, 195.
76. T. Murai, Y. Mutoh, S. Kato, Org. Lett. 2001, 3, 1993.
77. Selenoformaldehyde has been reported to be an unstable species, but can be trapped with dienes:
78. a) H. Bock, S. Aygen, P. Rosmus, B. Solouki, E. Weissflog, Chem. Ber. 1984, 117, 187.
79. b) R. H. Judge, D. C. Moule, J. Am. Chem. Soc. 1984, 106, 5406.
80. c) R. D. Brown, P. D. Godfrey, D. McNaughton, Chem. Phys. Lett. 1985, 118, 29.
81. d) G. A. Krafft, P. T. Meinke, J. Am. Chem. Soc. 1986, 108, 1314.
82. e) F. S. Guziec, Jr., L. J. Guziec, in Comprehensive Organic Functional Group Transformation, ed. by A. R. Katritzky, O. Meth-Cohn, C. W. Rees, Pergamon, Oxford, 1995, Vol. 3, pp. 381-401.