Alkynyltrifluoroborates as versatile tools in organic synthesis: A new route to spiroketals

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4909-4911

  Doubský, Jan ^a   Streinz, Ludvík ^a   Šaman, David ^a   Zedník, Jiří ^b   Koutek, Bohumír ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLTRIFLUOROBORATE; BORIC ACID; LACTONE; LITHIUM ALKYNYLTRIFLUOROBORATE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; HYDROGENATION; REACTION ANALYSIS;

BORON COMPOUNDS; CATALYSIS; CYCLIZATION; LITHIUM; MOLECULAR STRUCTURE; PALLADIUM; SPIRO COMPOUNDS;

EID: 12344282789     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047987k     Document Type: Article

References (28)

1. For recent reviews on the synthesis of spiroketals, see: (a) Pietruszka, J. Angew. Chem., Int. Ed. 1998, 37, 2629-2636. (b) Brimble, M. A.; Farès, F. A. Tetrahedron 1999, 55, 7661-7706. (c) Tu, Y. Q.; Hübener, A.; Zhang, Hesheng; Moore, Ch. J.; Fletcher, M. T.; Hayes, P.; Dettner, K.; Francke, W.; McErlean, Ch. S. P.; Kitching, W. Synthesis 2000, 1956-1978. (d) Francke, W.; Kitching, W. Curr. Org. Chem. 2001, 5, 233-251. (e) Mead, K. T.; Brewer, B. N. Curr. Org. Chem. 2003, 7, 227-256. (f) Brimble, M. A.; Furkert, D. P. Curr. Org. Chem. 2003, 7, 1461-1484.
2. For recent reviews on the synthesis of spiroketals, see: (a) Pietruszka, J. Angew. Chem., Int. Ed. 1998, 37, 2629-2636. (b) Brimble, M. A.; Farès, F. A. Tetrahedron 1999, 55, 7661-7706. (c) Tu, Y. Q.; Hübener, A.; Zhang, Hesheng; Moore, Ch. J.; Fletcher, M. T.; Hayes, P.; Dettner, K.; Francke, W.; McErlean, Ch. S. P.; Kitching, W. Synthesis 2000, 1956-1978. (d) Francke, W.; Kitching, W. Curr. Org. Chem. 2001, 5, 233-251. (e) Mead, K. T.; Brewer, B. N. Curr. Org. Chem. 2003, 7, 227-256. (f) Brimble, M. A.; Furkert, D. P. Curr. Org. Chem. 2003, 7, 1461-1484.
3. For recent reviews on the synthesis of spiroketals, see: (a) Pietruszka, J. Angew. Chem., Int. Ed. 1998, 37, 2629-2636. (b) Brimble, M. A.; Farès, F. A. Tetrahedron 1999, 55, 7661-7706. (c) Tu, Y. Q.; Hübener, A.; Zhang, Hesheng; Moore, Ch. J.; Fletcher, M. T.; Hayes, P.; Dettner, K.; Francke, W.; McErlean, Ch. S. P.; Kitching, W. Synthesis 2000, 1956-1978. (d) Francke, W.; Kitching, W. Curr. Org. Chem. 2001, 5, 233-251. (e) Mead, K. T.; Brewer, B. N. Curr. Org. Chem. 2003, 7, 227-256. (f) Brimble, M. A.; Furkert, D. P. Curr. Org. Chem. 2003, 7, 1461-1484.
4. For recent reviews on the synthesis of spiroketals, see: (a) Pietruszka, J. Angew. Chem., Int. Ed. 1998, 37, 2629-2636. (b) Brimble, M. A.; Farès, F. A. Tetrahedron 1999, 55, 7661-7706. (c) Tu, Y. Q.; Hübener, A.; Zhang, Hesheng; Moore, Ch. J.; Fletcher, M. T.; Hayes, P.; Dettner, K.; Francke, W.; McErlean, Ch. S. P.; Kitching, W. Synthesis 2000, 1956-1978. (d) Francke, W.; Kitching, W. Curr. Org. Chem. 2001, 5, 233-251. (e) Mead, K. T.; Brewer, B. N. Curr. Org. Chem. 2003, 7, 227-256. (f) Brimble, M. A.; Furkert, D. P. Curr. Org. Chem. 2003, 7, 1461-1484.
5. For recent reviews on the synthesis of spiroketals, see: (a) Pietruszka, J. Angew. Chem., Int. Ed. 1998, 37, 2629-2636. (b) Brimble, M. A.; Farès, F. A. Tetrahedron 1999, 55, 7661-7706. (c) Tu, Y. Q.; Hübener, A.; Zhang, Hesheng; Moore, Ch. J.; Fletcher, M. T.; Hayes, P.; Dettner, K.; Francke, W.; McErlean, Ch. S. P.; Kitching, W. Synthesis 2000, 1956-1978. (d) Francke, W.; Kitching, W. Curr. Org. Chem. 2001, 5, 233-251. (e) Mead, K. T.; Brewer, B. N. Curr. Org. Chem. 2003, 7, 227-256. (f) Brimble, M. A.; Furkert, D. P. Curr. Org. Chem. 2003, 7, 1461-1484.
6. For recent reviews on the synthesis of spiroketals, see: (a) Pietruszka, J. Angew. Chem., Int. Ed. 1998, 37, 2629-2636. (b) Brimble, M. A.; Farès, F. A. Tetrahedron 1999, 55, 7661-7706. (c) Tu, Y. Q.; Hübener, A.; Zhang, Hesheng; Moore, Ch. J.; Fletcher, M. T.; Hayes, P.; Dettner, K.; Francke, W.; McErlean, Ch. S. P.; Kitching, W. Synthesis 2000, 1956-1978. (d) Francke, W.; Kitching, W. Curr. Org. Chem. 2001, 5, 233-251. (e) Mead, K. T.; Brewer, B. N. Curr. Org. Chem. 2003, 7, 227-256. (f) Brimble, M. A.; Furkert, D. P. Curr. Org. Chem. 2003, 7, 1461-1484.
7. For selected recent examples of spiroketal syntheses, see: (a) Hao, J.; Forsyth, C. J. Tetrahedron Lett. 2002, 43, 1-2. (b) Sartillo-Piscil, F.; Vargas, M.; de Parrodi, C. A.; Quintero, L. Tetraheron Lett. 2003, 44, 3919-3921. (c) Tsang, K. I.; Brimble, M. A.; Bremner, J. B. Org. Lett. 2003, 5, 4425-4427. (d) Alonso, F.; Meléndes, J.; Yus, M. Tetrahedron Lett. 2004, 45, 1717-1720. (e) Wang, L.; Floreancig, P. E. Org. Lett. 2004, 6, 569-572. (f) Ghosh, S. K.; Hsung, R. P.; Wang, J. Tetrahedron Lett. 2004, 45, 5505-5510.
8. For selected recent examples of spiroketal syntheses, see: (a) Hao, J.; Forsyth, C. J. Tetrahedron Lett. 2002, 43, 1-2. (b) Sartillo-Piscil, F.; Vargas, M.; de Parrodi, C. A.; Quintero, L. Tetraheron Lett. 2003, 44, 3919-3921. (c) Tsang, K. I.; Brimble, M. A.; Bremner, J. B. Org. Lett. 2003, 5, 4425-4427. (d) Alonso, F.; Meléndes, J.; Yus, M. Tetrahedron Lett. 2004, 45, 1717-1720. (e) Wang, L.; Floreancig, P. E. Org. Lett. 2004, 6, 569-572. (f) Ghosh, S. K.; Hsung, R. P.; Wang, J. Tetrahedron Lett. 2004, 45, 5505-5510.
9. For selected recent examples of spiroketal syntheses, see: (a) Hao, J.; Forsyth, C. J. Tetrahedron Lett. 2002, 43, 1-2. (b) Sartillo-Piscil, F.; Vargas, M.; de Parrodi, C. A.; Quintero, L. Tetraheron Lett. 2003, 44, 3919-3921. (c) Tsang, K. I.; Brimble, M. A.; Bremner, J. B. Org. Lett. 2003, 5, 4425-4427. (d) Alonso, F.; Meléndes, J.; Yus, M. Tetrahedron Lett. 2004, 45, 1717-1720. (e) Wang, L.; Floreancig, P. E. Org. Lett. 2004, 6, 569-572. (f) Ghosh, S. K.; Hsung, R. P.; Wang, J. Tetrahedron Lett. 2004, 45, 5505-5510.
10. For selected recent examples of spiroketal syntheses, see: (a) Hao, J.; Forsyth, C. J. Tetrahedron Lett. 2002, 43, 1-2. (b) Sartillo-Piscil, F.; Vargas, M.; de Parrodi, C. A.; Quintero, L. Tetraheron Lett. 2003, 44, 3919-3921. (c) Tsang, K. I.; Brimble, M. A.; Bremner, J. B. Org. Lett. 2003, 5, 4425-4427. (d) Alonso, F.; Meléndes, J.; Yus, M. Tetrahedron Lett. 2004, 45, 1717-1720. (e) Wang, L.; Floreancig, P. E. Org. Lett. 2004, 6, 569-572. (f) Ghosh, S. K.; Hsung, R. P.; Wang, J. Tetrahedron Lett. 2004, 45, 5505-5510.
11. For selected recent examples of spiroketal syntheses, see: (a) Hao, J.; Forsyth, C. J. Tetrahedron Lett. 2002, 43, 1-2. (b) Sartillo-Piscil, F.; Vargas, M.; de Parrodi, C. A.; Quintero, L. Tetraheron Lett. 2003, 44, 3919-3921. (c) Tsang, K. I.; Brimble, M. A.; Bremner, J. B. Org. Lett. 2003, 5, 4425-4427. (d) Alonso, F.; Meléndes, J.; Yus, M. Tetrahedron Lett. 2004, 45, 1717-1720. (e) Wang, L.; Floreancig, P. E. Org. Lett. 2004, 6, 569-572. (f) Ghosh, S. K.; Hsung, R. P.; Wang, J. Tetrahedron Lett. 2004, 45, 5505-5510.
12. For selected recent examples of spiroketal syntheses, see: (a) Hao, J.; Forsyth, C. J. Tetrahedron Lett. 2002, 43, 1-2. (b) Sartillo-Piscil, F.; Vargas, M.; de Parrodi, C. A.; Quintero, L. Tetraheron Lett. 2003, 44, 3919-3921. (c) Tsang, K. I.; Brimble, M. A.; Bremner, J. B. Org. Lett. 2003, 5, 4425-4427. (d) Alonso, F.; Meléndes, J.; Yus, M. Tetrahedron Lett. 2004, 45, 1717-1720. (e) Wang, L.; Floreancig, P. E. Org. Lett. 2004, 6, 569-572. (f) Ghosh, S. K.; Hsung, R. P.; Wang, J. Tetrahedron Lett. 2004, 45, 5505-5510.
13. (a) Katritzky, A. R.; Lang, H. J. Org. Chem. 1995, 60, 7612-7618.
14. (b) Chowdhury, C.; Kundu, N. G. Tetrahedron 1999, 55, 7011-7016.
15. (c) Kakino, R.; Narahashi, H.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2002, 75, 1333-1345.
16. (d) Alonso, D. A.; Nájera, C.; Pacheco, M. C. J. Org. Chem. 2004, 69, 1615-1619.
17. (e) Chen, L.; Li, Ch.-J. Org. Lett. 2004, 6, 3151-3153 and references therein.
18. Brown, H. C.; Racherla, U. S.; Singh, S. M. Tetrahedron Lett. 1984, 25, 2411-2414.
19. (a) Yamaguchi, M.; Shibato, K.; Fujiwara, S.; Hirao, I. Synthesis 1986, 421-422.
20. (b) Krafft, M. E.; Bonaga, L. V. R.; Felts, A. S.; Hirosawa, Ch.; Kerrigan, S. J. Org. Chem. 2003, 68, 6039-6042.
21. Doubský, J.; Streinz, L.; Lešetický, L.; Koutek, B. Synlett 2003, 937-942.
22. Jacobson, R.; Taylor, R. J.; Williams, H. J.; Smith, L. R. J. Org. Chem. 1982, 47, 3140-3142.
23. Secrist, J. A.; Logue, M. W. J. Org. Chem. 1972, 37, 335-336.
24. Itoh, A.; Kodama, T.; Maeda, S.; Masaki, Y. Tetrahedron Lett. 1998, 39, 9461-9464.
25. (a) Phillips, C.; Jacobson, R.; Abrahams, B.; Williams, H. J.; Smith, L. R. J. Org. Chem. 1980, 45, 1920-1924.
26. (b) Mudryk, B.; Shook, C. A.; Cohen, T. J. Am. Chem. Soc. 1990, 112, 6389-6391.
27. (c) Shimizu, Y.; Kiyota, H.; Oritani, T. Tetrahedron Lett. 2000, 41, 3141-3144.
28. (d) Hayes, P.; Fletcher, M. Y.; Moore, Ch. J.; Kitching, W. J. Org. Chem. 2001, 66, 2530-2533.