Reactions of Vinyl Sulfoxides with Magnesium Amides. One-Pot Synthesis of Symmetrical and Unsymmetrical β-(Dialkylamino) Dithioacetals

Journal of Organic Chemistry

Volumn 62, Issue 23, 1997, Pages 8015-8017

  Kawakita, Masataka ^a   Yokota, Kouichi ^a   Akamatsu, Hideki ^a   Irisawa, Susumu ^a   Morikawa, Osamu ^a   Konishi, Hisatoshi ^a   Kobayashi, Kazuhiro ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343611922     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970741r     Document Type: Article

References (28)

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3. Green, M. B.; Jenkins, W. L. J. Sci. Food Agric. 1958, 536. Japan Soda Co., Ltd., Japan Patent 5699 1963; Chem. Abstr. 1864, 60, 4720h.
4. Green, M. B.; Jenkins, W. L. J. Sci. Food Agric. 1958, 536. Japan Soda Co., Ltd., Japan Patent 5699 1963; Chem. Abstr. 1864, 60, 4720h.
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7. (b) Kobayashi, K.; Yokota, K.; Akamatsu, H.; Morikawa, O.; Konishi, H. Bull. Chem. Soc. Jpn. 1996, 69, 441.
8. Kobayashi, K.; Kawakita, M.; Akamatsu, H.; Morikawa, O.; Konishi, H. Bull. Chem. Soc. Jpn. 1996, 69, 2645.
9. For reported examples of additive Pummerer-type reactions, see: Russell, G. A.; Sabourin, E.; Mikol, G. J. J. Org. Chem. 1966, 31, 2854. Miyamoto, N.; Fukuoka, D.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1974, 47, 1817. Kosugi, H.; Uda, H.; Yamagiwa, S. J. Chem. Soc., Chem. Commun. 1976, 71. Reamonn, L. S. S.; O'Sullivan, W. I. J. Chem. Soc., Chem. Commun. 1976, 642. King, R. R. J. Org. Chem. 1978, 43, 1262. Marino, J. P.; Neisser, M. J. Am. Chem. Soc. 1981, 103, 7687. Posner, G. H.; Asirvatham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 542. Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Miki, T.; Tamura, Y. Chem. Pharm. Bull. 1987, 35, 3623. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 31, 6441. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 32, 6973.
10. For reported examples of additive Pummerer-type reactions, see: Russell, G. A.; Sabourin, E.; Mikol, G. J. J. Org. Chem. 1966, 31, 2854. Miyamoto, N.; Fukuoka, D.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1974, 47, 1817. Kosugi, H.; Uda, H.; Yamagiwa, S. J. Chem. Soc., Chem. Commun. 1976, 71. Reamonn, L. S. S.; O'Sullivan, W. I. J. Chem. Soc., Chem. Commun. 1976, 642. King, R. R. J. Org. Chem. 1978, 43, 1262. Marino, J. P.; Neisser, M. J. Am. Chem. Soc. 1981, 103, 7687. Posner, G. H.; Asirvatham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 542. Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Miki, T.; Tamura, Y. Chem. Pharm. Bull. 1987, 35, 3623. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 31, 6441. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 32, 6973.
11. For reported examples of additive Pummerer-type reactions, see: Russell, G. A.; Sabourin, E.; Mikol, G. J. J. Org. Chem. 1966, 31, 2854. Miyamoto, N.; Fukuoka, D.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1974, 47, 1817. Kosugi, H.; Uda, H.; Yamagiwa, S. J. Chem. Soc., Chem. Commun. 1976, 71. Reamonn, L. S. S.; O'Sullivan, W. I. J. Chem. Soc., Chem. Commun. 1976, 642. King, R. R. J. Org. Chem. 1978, 43, 1262. Marino, J. P.; Neisser, M. J. Am. Chem. Soc. 1981, 103, 7687. Posner, G. H.; Asirvatham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 542. Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Miki, T.; Tamura, Y. Chem. Pharm. Bull. 1987, 35, 3623. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 31, 6441. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 32, 6973.
12. For reported examples of additive Pummerer-type reactions, see: Russell, G. A.; Sabourin, E.; Mikol, G. J. J. Org. Chem. 1966, 31, 2854. Miyamoto, N.; Fukuoka, D.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1974, 47, 1817. Kosugi, H.; Uda, H.; Yamagiwa, S. J. Chem. Soc., Chem. Commun. 1976, 71. Reamonn, L. S. S.; O'Sullivan, W. I. J. Chem. Soc., Chem. Commun. 1976, 642. King, R. R. J. Org. Chem. 1978, 43, 1262. Marino, J. P.; Neisser, M. J. Am. Chem. Soc. 1981, 103, 7687. Posner, G. H.; Asirvatham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 542. Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Miki, T.; Tamura, Y. Chem. Pharm. Bull. 1987, 35, 3623. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 31, 6441. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 32, 6973.
13. For reported examples of additive Pummerer-type reactions, see: Russell, G. A.; Sabourin, E.; Mikol, G. J. J. Org. Chem. 1966, 31, 2854. Miyamoto, N.; Fukuoka, D.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1974, 47, 1817. Kosugi, H.; Uda, H.; Yamagiwa, S. J. Chem. Soc., Chem. Commun. 1976, 71. Reamonn, L. S. S.; O'Sullivan, W. I. J. Chem. Soc., Chem. Commun. 1976, 642. King, R. R. J. Org. Chem. 1978, 43, 1262. Marino, J. P.; Neisser, M. J. Am. Chem. Soc. 1981, 103, 7687. Posner, G. H.; Asirvatham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 542. Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Miki, T.; Tamura, Y. Chem. Pharm. Bull. 1987, 35, 3623. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 31, 6441. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 32, 6973.
14. For reported examples of additive Pummerer-type reactions, see: Russell, G. A.; Sabourin, E.; Mikol, G. J. J. Org. Chem. 1966, 31, 2854. Miyamoto, N.; Fukuoka, D.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1974, 47, 1817. Kosugi, H.; Uda, H.; Yamagiwa, S. J. Chem. Soc., Chem. Commun. 1976, 71. Reamonn, L. S. S.; O'Sullivan, W. I. J. Chem. Soc., Chem. Commun. 1976, 642. King, R. R. J. Org. Chem. 1978, 43, 1262. Marino, J. P.; Neisser, M. J. Am. Chem. Soc. 1981, 103, 7687. Posner, G. H.; Asirvatham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 542. Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Miki, T.; Tamura, Y. Chem. Pharm. Bull. 1987, 35, 3623. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 31, 6441. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 32, 6973.
15. For reported examples of additive Pummerer-type reactions, see: Russell, G. A.; Sabourin, E.; Mikol, G. J. J. Org. Chem. 1966, 31, 2854. Miyamoto, N.; Fukuoka, D.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1974, 47, 1817. Kosugi, H.; Uda, H.; Yamagiwa, S. J. Chem. Soc., Chem. Commun. 1976, 71. Reamonn, L. S. S.; O'Sullivan, W. I. J. Chem. Soc., Chem. Commun. 1976, 642. King, R. R. J. Org. Chem. 1978, 43, 1262. Marino, J. P.; Neisser, M. J. Am. Chem. Soc. 1981, 103, 7687. Posner, G. H.; Asirvatham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 542. Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Miki, T.; Tamura, Y. Chem. Pharm. Bull. 1987, 35, 3623. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 31, 6441. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 32, 6973.
16. For reported examples of additive Pummerer-type reactions, see: Russell, G. A.; Sabourin, E.; Mikol, G. J. J. Org. Chem. 1966, 31, 2854. Miyamoto, N.; Fukuoka, D.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1974, 47, 1817. Kosugi, H.; Uda, H.; Yamagiwa, S. J. Chem. Soc., Chem. Commun. 1976, 71. Reamonn, L. S. S.; O'Sullivan, W. I. J. Chem. Soc., Chem. Commun. 1976, 642. King, R. R. J. Org. Chem. 1978, 43, 1262. Marino, J. P.; Neisser, M. J. Am. Chem. Soc. 1981, 103, 7687. Posner, G. H.; Asirvatham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 542. Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Miki, T.; Tamura, Y. Chem. Pharm. Bull. 1987, 35, 3623. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 31, 6441. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 32, 6973.
17. For reported examples of additive Pummerer-type reactions, see: Russell, G. A.; Sabourin, E.; Mikol, G. J. J. Org. Chem. 1966, 31, 2854. Miyamoto, N.; Fukuoka, D.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1974, 47, 1817. Kosugi, H.; Uda, H.; Yamagiwa, S. J. Chem. Soc., Chem. Commun. 1976, 71. Reamonn, L. S. S.; O'Sullivan, W. I. J. Chem. Soc., Chem. Commun. 1976, 642. King, R. R. J. Org. Chem. 1978, 43, 1262. Marino, J. P.; Neisser, M. J. Am. Chem. Soc. 1981, 103, 7687. Posner, G. H.; Asirvatham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 542. Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Miki, T.; Tamura, Y. Chem. Pharm. Bull. 1987, 35, 3623. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 31, 6441. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 32, 6973.
18. For reported examples of additive Pummerer-type reactions, see: Russell, G. A.; Sabourin, E.; Mikol, G. J. J. Org. Chem. 1966, 31, 2854. Miyamoto, N.; Fukuoka, D.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1974, 47, 1817. Kosugi, H.; Uda, H.; Yamagiwa, S. J. Chem. Soc., Chem. Commun. 1976, 71. Reamonn, L. S. S.; O'Sullivan, W. I. J. Chem. Soc., Chem. Commun. 1976, 642. King, R. R. J. Org. Chem. 1978, 43, 1262. Marino, J. P.; Neisser, M. J. Am. Chem. Soc. 1981, 103, 7687. Posner, G. H.; Asirvatham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 542. Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Miki, T.; Tamura, Y. Chem. Pharm. Bull. 1987, 35, 3623. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 31, 6441. Craig, D.; Daniels, K.; Mackenzie, A. R. Tetrahedron Lett. 1991, 32, 6973.
19. We observed that the yields of the products decreased with smaller molar amounts of either of ethylmagnesium bromide or secondary amines.
20. (a) The clear addition of the amide 7 to the vinyl sulfoxide 1 may be explained by a six-membered ring intermediate.
21. (b) The addition of 7 to the sulfonium ion 9 did not occur, most probably due to the steric hindrance of 7.
22. Only a trace amount of the symmetrical dithioacetal 3a was obtained in each reaction. This indicates that the rate of addition of the thiolate anion to 9 was much faster than that of formation of the β-aminoalkyl sulfide 11, the interaction of which with 9 leads to 3a.
23. Craig, C.; Daniels, K.; Marsch, A.; Rainford, D.; Smith, A. M. Synlett 1990, 531.
24. Williams, R. V.; Chauhan, K. J. Chem. Soc., Chem. Commun. 1991, 1672.
25. Shelton, J. R.; Davis, K. E. Int. J. Sulfur Chem. 1973, 3, 205; Chem. Abstr. 1973, 79, 125593h.
26. Shelton, J. R.; Davis, K. E. Int. J. Sulfur Chem. 1973, 3, 205; Chem. Abstr. 1973, 79, 125593h.
27. (a) Werner, E. G. G. Recl. Trav. Chim. Pays-Bas 1949, 68, 1509.
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