A new reaction of imines with alkynyl sulfides affording α,β-unsaturated thioimidates

Journal of Organic Chemistry

Volumn 61, Issue 6, 1996, Pages 1902-1903

  Ishitani, Haruro ^a   Nagayama, Satoshi ^a   Kobayashi, Shu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001044209     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951924l     Document Type: Article

References (24)

1. (a) The Chemistry of the Amidines and Imidates; Patai, S., Ed.; John Wiley and Sons: New York, 1975.
2. (b) Roger, R.; Neilson, D. G. Chem. Rev. 1961, 61, 179.
3. Yoshida, H.; Ogata, T.; Inokawa, S. Bull. Chem. Soc. Jpn. 1977, 50, 3315.
4. (a) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I Synlett 1995, 233.
5. (b) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773.
6. (a) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423.
7. (b) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195.
8. Boger, D. L.; Weinreb, S. M. Hetero Diets-Alder Methodology in Organic Synthesis; Academic Press: London, 1987.
9. Cf. Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801.
10. 2 as a catalyst. Narasaka, K.; Shibata, T. Heterocycles 1993, 35 1039.
11. The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
12. Arena and Bos et al. reported that the reactions of aldehydes or ketones with alkynyl ethers or alkynyl sulfides afforded α,β-unsaturated esters or α,β-unsaturated thioesters in the presence of a stoichiometric amount of a Lewis acid (a) Vieregge, H.; Schmidt, H. M.; Renema, J.; Bos, H. J. T.; Arens, J. F. Rec. Trav. Chim. 1966, 85, 929. (b) Bos, H. J. T.; Boleij, J. Rec. Trav. Chim. 1969, 88, 465 and references cited therein. See also: (c) Hayashi, A.; Yamaguchi, M.; Hirama, M. Synlett 1995, 195. (d) Fischer, H.; Tiriliomis, A.; Gerbing, U.; Huber, B.; Muller, G. J. Chem. Soc., Chem. Commun. 1987, 559. (e) Elferink, V. H. M.; Visser, R. G.; Bos, H. J. T. Rec. Trav. Chim. Pays-Bas 1981, 100, 414.
13. Arena and Bos et al. reported that the reactions of aldehydes or ketones with alkynyl ethers or alkynyl sulfides afforded α,β-unsaturated esters or α,β-unsaturated thioesters in the presence of a stoichiometric amount of a Lewis acid (a) Vieregge, H.; Schmidt, H. M.; Renema, J.; Bos, H. J. T.; Arens, J. F. Rec. Trav. Chim. 1966, 85, 929. (b) Bos, H. J. T.; Boleij, J. Rec. Trav. Chim. 1969, 88, 465 and references cited therein. See also: (c) Hayashi, A.; Yamaguchi, M.; Hirama, M. Synlett 1995, 195. (d) Fischer, H.; Tiriliomis, A.; Gerbing, U.; Huber, B.; Muller, G. J. Chem. Soc., Chem. Commun. 1987, 559. (e) Elferink, V. H. M.; Visser, R. G.; Bos, H. J. T. Rec. Trav. Chim. Pays-Bas 1981, 100, 414.
14. Arena and Bos et al. reported that the reactions of aldehydes or ketones with alkynyl ethers or alkynyl sulfides afforded α,β-unsaturated esters or α,β-unsaturated thioesters in the presence of a stoichiometric amount of a Lewis acid (a) Vieregge, H.; Schmidt, H. M.; Renema, J.; Bos, H. J. T.; Arens, J. F. Rec. Trav. Chim. 1966, 85, 929. (b) Bos, H. J. T.; Boleij, J. Rec. Trav. Chim. 1969, 88, 465 and references cited therein. See also: (c) Hayashi, A.; Yamaguchi, M.; Hirama, M. Synlett 1995, 195. (d) Fischer, H.; Tiriliomis, A.; Gerbing, U.; Huber, B.; Muller, G. J. Chem. Soc., Chem. Commun. 1987, 559. (e) Elferink, V. H. M.; Visser, R. G.; Bos, H. J. T. Rec. Trav. Chim. Pays-Bas 1981, 100, 414.
15. Arena and Bos et al. reported that the reactions of aldehydes or ketones with alkynyl ethers or alkynyl sulfides afforded α,β-unsaturated esters or α,β-unsaturated thioesters in the presence of a stoichiometric amount of a Lewis acid (a) Vieregge, H.; Schmidt, H. M.; Renema, J.; Bos, H. J. T.; Arens, J. F. Rec. Trav. Chim. 1966, 85, 929. (b) Bos, H. J. T.; Boleij, J. Rec. Trav. Chim. 1969, 88, 465 and references cited therein. See also: (c) Hayashi, A.; Yamaguchi, M.; Hirama, M. Synlett 1995, 195. (d) Fischer, H.; Tiriliomis, A.; Gerbing, U.; Huber, B.; Muller, G. J. Chem. Soc., Chem. Commun. 1987, 559. (e) Elferink, V. H. M.; Visser, R. G.; Bos, H. J. T. Rec. Trav. Chim. Pays-Bas 1981, 100, 414.
16. Arena and Bos et al. reported that the reactions of aldehydes or ketones with alkynyl ethers or alkynyl sulfides afforded α,β-unsaturated esters or α,β-unsaturated thioesters in the presence of a stoichiometric amount of a Lewis acid (a) Vieregge, H.; Schmidt, H. M.; Renema, J.; Bos, H. J. T.; Arens, J. F. Rec. Trav. Chim. 1966, 85, 929. (b) Bos, H. J. T.; Boleij, J. Rec. Trav. Chim. 1969, 88, 465 and references cited therein. See also: (c) Hayashi, A.; Yamaguchi, M.; Hirama, M. Synlett 1995, 195. (d) Fischer, H.; Tiriliomis, A.; Gerbing, U.; Huber, B.; Muller, G. J. Chem. Soc., Chem. Commun. 1987, 559. (e) Elferink, V. H. M.; Visser, R. G.; Bos, H. J. T. Rec. Trav. Chim. Pays-Bas 1981, 100, 414.
17. It was reported that ynamines added to imines in moderate yields in the absence of Lewis acids. Fuks, R.; Viehe, H. G. Chem. Ber. 1970, 103, 573.
18. 4) and evaporated, the crude product was chromatographed on silica gel to afford the corresponding α,β-unsaturated thioimidate 3. The catalyst was quantitatively recovered from the aqueous layer and could be reused for further runs.
19. Albrecht, R.; Kresze, G.; Mlakar, B. Chem. Ber 1964, 97, 1483.
20. Kobayashi, S Synlett 1994, 689.
21. Cf. (a) Warreher, R. N.; Kretschmer, G. J. Chem Soc., Chem. Commun. 1977, 806. See also: (b) Friedrich, L. E.; Bower, J D. J. Am. Chem. Soc. 1973, 95, 6869. (c) Friedrich, L. E.; Lam, D. Y.-S. J Org. Chem. 1981, 46, 306. (d) Martino, P. C.; Shevlin, P. B. J. Am. Chem. Soc. 1980, 102, 5429 and references cited therein.
22. Cf. (a) Warreher, R. N.; Kretschmer, G. J. Chem Soc., Chem. Commun. 1977, 806. See also: (b) Friedrich, L. E.; Bower, J D. J. Am. Chem. Soc. 1973, 95, 6869. (c) Friedrich, L. E.; Lam, D. Y.-S. J Org. Chem. 1981, 46, 306. (d) Martino, P. C.; Shevlin, P. B. J. Am. Chem. Soc. 1980, 102, 5429 and references cited therein.
23. Cf. (a) Warreher, R. N.; Kretschmer, G. J. Chem Soc., Chem. Commun. 1977, 806. See also: (b) Friedrich, L. E.; Bower, J D. J. Am. Chem. Soc. 1973, 95, 6869. (c) Friedrich, L. E.; Lam, D. Y.-S. J Org. Chem. 1981, 46, 306. (d) Martino, P. C.; Shevlin, P. B. J. Am. Chem. Soc. 1980, 102, 5429 and references cited therein.
24. Cf. (a) Warreher, R. N.; Kretschmer, G. J. Chem Soc., Chem. Commun. 1977, 806. See also: (b) Friedrich, L. E.; Bower, J D. J. Am. Chem. Soc. 1973, 95, 6869. (c) Friedrich, L. E.; Lam, D. Y.-S. J Org. Chem. 1981, 46, 306. (d) Martino, P. C.; Shevlin, P. B. J. Am. Chem. Soc. 1980, 102, 5429 and references cited therein.