Silver-catalyzed [2 + 2] cycloadditions of siloxy alkynes

Journal of the American Chemical Society

Volumn 126, Issue 24, 2004, Pages 7442-7443

  Sweis, Randy F ^a   Schramm, Michael P ^a   Kozmin, Sergey A ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; LEWIS ACID; SILOXANE; SILVER;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLOADDITION; ENANTIOSELECTIVITY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

ALKYNES; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; SILVER;

EID: 2942687050     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048251l     Document Type: Article

References (27)

1. (a) Yanagisawa, A.; Nakashima, H.; Ashiba, I.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723.
2. (b) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
3. (c) Wei, C.; Li, Z.; Li, C. J. Org. Lett. 2003, 5, 4473.
4. (d) Josephsohn, N. S.; Snapper, M. C.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 4018.
5. (e) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038.
6. (a) Cirakovic, J.; Driver, T. G.; Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 9370.
7. (b) Dias, H. V. R.; Browning, R. G.; Polach, S. A.; Diyabalanage, H. V. K.; Lovely, C. J. J. Am. Chem. Soc. 2003, 125, 9270.
8. (c) Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202.
9. Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274.
10. For a recent review of ynolates, see: Shindo, M. Synthesis 2003, 2275.
11. There are two reports describing Lewis acid-promoted reactions of siloxy alkynes with aldehydes and imines: (a) Kowalski, C. J.; Sakdarat, S. J. Org. Chem. 1990, 55, 1977.
12. (b) Shindo, M.; Oya, S.; Sato, Y.; Shishido, K. Heterocycles 2000, 52, 545.
13. Ficini, J. Tetrahedron 1976, 32, 1449.
14. (a) Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Niihata, S. J. Am. Chem. Soc. 1992, 114, 8869.
15. (b) During the submission of the present manuscript, the Cu-catalyzed asymmetric [2 + 2] cycloaddition of alkynyl sulfides was reported: Ito, H.; Hasegawa, M.; Takenaka, Y.; Kobayashi, T.; Iguchi, K. J. Am. Chem. Soc. 2004, 126, 4520.
16. For selected examples, see: (a) Noyori, R.; Ishigami, T.; Hayashi, N.; Takaya, H. J. Am. Chem. Soc. 1973, 95, 1674.
17. (b) Mitsudo, T.; Naruse, H.; Kondo, T.; Ozaki, Y.; Watenabe, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 580.
18. (c) Baik, T.-G.; Lusi, A. L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 6716.
19. For thermal cycloadditions of siloxy alkynes with ketenes, see: (a) Danheiser, R. L.; Gee, S. K. J. Org. Chem. 1984, 49, 1672.
20. (b) Danheiser, R. L.; Gee, S. K.; Perez, J. J. J. Am. Chem. Soc. 1986, 108, 806.
21. (c) Kowalski, C. J.; Lal, G. S. J. Am. Chem. Soc. 1988, 110, 3693.
22. 2, see: Vij, A.; Zheng, Y. Y.; Kirchmeier, R. L.; Shreeve, J. M. Inorg. Chem. 1994, 33, 3281.
23. 2 for 30 min at 20 °C.
24. For chemical shift changes upon complexation of alkynes and alkenes to Ag(I) ions, see: Lewandos, G. S.; Gregston, D. K. Nelson, F. R. J. Organomet. Chem. 1976, 118, 363.
25. Takani, K.; Ueno, M.; lnanaga, K.; Ihara, M. J. Org. Chem. 2004, 69, 517 and references therein.
26. For potentially mechanistically related Ni(0)-catalyzed reactions of alkynes with enones and aldehydes, see; (a) Montgomery, J. Acc. Chem. Res. 2000, 33, 467.
27. (b) Miller, K. M.; Huang, W. S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442 and references therein.