Stereoselective alkynylation of trans-2,3-epoxy sulfides with double inversion of configuration by alkynylaluminums

Tetrahedron Letters

Volumn 40, Issue 52, 1999, Pages 9267-9270

  Sasaki, Minoru ^a   Miyazawa, Masahiro ^a   Tanino, Keiji ^a   Miyashita, Masaaki ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Alkynes; Aluminum; Aluminum compounds; Epoxides; Stereocontrol; Sulfides

Indexed keywords

ALKYNE DERIVATIVE; ALUMINUM; ALUMINUM DERIVATIVE; EPOXIDE; SULFIDE;

ARTICLE; CHEMICAL MODIFICATION; STEREOCHEMISTRY;

EID: 0033601444     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02013-4     Document Type: Article

References (21)

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2. Posner, G. H. Org. React. 1975, 22, 253-400; Ma, P.; Martin, V.S.; Masamune, S.; Sharpless, K. B.; Viti, S. M. J. Org. Chem. 1982, 47, 1378-1380; Suzuki, T.; Saimoto, H.; Tomioka, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 3597-3600; Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A.; Parker, D. J. Org. Chem. 1984, 49, 3928-3938; Onaka, M.; Sugita, K.; Takeuchi, H.; Izumi, Y. J. Chem. Soc., Chem. Commun. 1988, 1173-1174; Comprehensive Organic Synthesis; Trost, B. M., Ed.; Vol. 3; Carbon-Carbon σ-Bond Formation; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Bonini, C.; Righi, G. Synthesis 1994, 225-238.
3. Posner, G. H. Org. React. 1975, 22, 253-400; Ma, P.; Martin, V.S.; Masamune, S.; Sharpless, K. B.; Viti, S. M. J. Org. Chem. 1982, 47, 1378-1380; Suzuki, T.; Saimoto, H.; Tomioka, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 3597-3600; Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A.; Parker, D. J. Org. Chem. 1984, 49, 3928-3938; Onaka, M.; Sugita, K.; Takeuchi, H.; Izumi, Y. J. Chem. Soc., Chem. Commun. 1988, 1173-1174; Comprehensive Organic Synthesis; Trost, B. M., Ed.; Vol. 3; Carbon-Carbon σ-Bond Formation; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Bonini, C.; Righi, G. Synthesis 1994, 225-238.
4. Posner, G. H. Org. React. 1975, 22, 253-400; Ma, P.; Martin, V.S.; Masamune, S.; Sharpless, K. B.; Viti, S. M. J. Org. Chem. 1982, 47, 1378-1380; Suzuki, T.; Saimoto, H.; Tomioka, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 3597-3600; Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A.; Parker, D. J. Org. Chem. 1984, 49, 3928-3938; Onaka, M.; Sugita, K.; Takeuchi, H.; Izumi, Y. J. Chem. Soc., Chem. Commun. 1988, 1173-1174; Comprehensive Organic Synthesis; Trost, B. M., Ed.; Vol. 3; Carbon-Carbon σ-Bond Formation; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Bonini, C.; Righi, G. Synthesis 1994, 225-238.
5. Posner, G. H. Org. React. 1975, 22, 253-400; Ma, P.; Martin, V.S.; Masamune, S.; Sharpless, K. B.; Viti, S. M. J. Org. Chem. 1982, 47, 1378-1380; Suzuki, T.; Saimoto, H.; Tomioka, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 3597-3600; Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A.; Parker, D. J. Org. Chem. 1984, 49, 3928-3938; Onaka, M.; Sugita, K.; Takeuchi, H.; Izumi, Y. J. Chem. Soc., Chem. Commun. 1988, 1173-1174; Comprehensive Organic Synthesis; Trost, B. M., Ed.; Vol. 3; Carbon-Carbon σ-Bond Formation; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Bonini, C.; Righi, G. Synthesis 1994, 225-238.
6. Posner, G. H. Org. React. 1975, 22, 253-400; Ma, P.; Martin, V.S.; Masamune, S.; Sharpless, K. B.; Viti, S. M. J. Org. Chem. 1982, 47, 1378-1380; Suzuki, T.; Saimoto, H.; Tomioka, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 3597-3600; Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A.; Parker, D. J. Org. Chem. 1984, 49, 3928-3938; Onaka, M.; Sugita, K.; Takeuchi, H.; Izumi, Y. J. Chem. Soc., Chem. Commun. 1988, 1173-1174; Comprehensive Organic Synthesis; Trost, B. M., Ed.; Vol. 3; Carbon-Carbon σ-Bond Formation; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Bonini, C.; Righi, G. Synthesis 1994, 225-238.
7. Posner, G. H. Org. React. 1975, 22, 253-400; Ma, P.; Martin, V.S.; Masamune, S.; Sharpless, K. B.; Viti, S. M. J. Org. Chem. 1982, 47, 1378-1380; Suzuki, T.; Saimoto, H.; Tomioka, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 3597-3600; Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A.; Parker, D. J. Org. Chem. 1984, 49, 3928-3938; Onaka, M.; Sugita, K.; Takeuchi, H.; Izumi, Y. J. Chem. Soc., Chem. Commun. 1988, 1173-1174; Comprehensive Organic Synthesis; Trost, B. M., Ed.; Vol. 3; Carbon-Carbon σ-Bond Formation; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Bonini, C.; Righi, G. Synthesis 1994, 225-238.
8. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions of epoxides: Kudo, K.; Saigo, K.; Hashimoto, Y.; Saito, K.; Hasegawa, M. Chem. Lett. 1992, 1449-1452; Kudo, K.; Hashimoto, Y.; Houchigai, H.; Hasegawa, M.; Saigo, K. Bull. Chem. Soc. Jpn. 1993, 66, 848-856; Kudo, K.; Hashimoto, Y.; Sukegawa, M.; Hasegawa, M.; Saigo, K. J. Org. Chem. 1993, 58, 579-857; Hashimoto, Y.; Sato, Y.; Takeshita, N.; Kudo, K.; Saigo, K. Tetrahedron 1994, 50, 8317-8336; Miyauchi, H.; Nakamura, T.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 1731-1737; Miyauchi, H.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 3591-3598; Liu, C.; Kudo, K.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1996, 61, 494-502; Liu, C.; Hashimoto, Y.; Saigo, K. Tetrahedron Lett. 1996, 37, 6177-6180; Gill, D. M.; Pegg, N. A.; Rayner, C. M. Tetrahedron 1996, 52, 3609-3630.
9. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions of epoxides: Kudo, K.; Saigo, K.; Hashimoto, Y.; Saito, K.; Hasegawa, M. Chem. Lett. 1992, 1449-1452; Kudo, K.; Hashimoto, Y.; Houchigai, H.; Hasegawa, M.; Saigo, K. Bull. Chem. Soc. Jpn. 1993, 66, 848-856; Kudo, K.; Hashimoto, Y.; Sukegawa, M.; Hasegawa, M.; Saigo, K. J. Org. Chem. 1993, 58, 579-857; Hashimoto, Y.; Sato, Y.; Takeshita, N.; Kudo, K.; Saigo, K. Tetrahedron 1994, 50, 8317-8336; Miyauchi, H.; Nakamura, T.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 1731-1737; Miyauchi, H.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 3591-3598; Liu, C.; Kudo, K.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1996, 61, 494-502; Liu, C.; Hashimoto, Y.; Saigo, K. Tetrahedron Lett. 1996, 37, 6177-6180; Gill, D. M.; Pegg, N. A.; Rayner, C. M. Tetrahedron 1996, 52, 3609-3630.
10. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions of epoxides: Kudo, K.; Saigo, K.; Hashimoto, Y.; Saito, K.; Hasegawa, M. Chem. Lett. 1992, 1449-1452; Kudo, K.; Hashimoto, Y.; Houchigai, H.; Hasegawa, M.; Saigo, K. Bull. Chem. Soc. Jpn. 1993, 66, 848-856; Kudo, K.; Hashimoto, Y.; Sukegawa, M.; Hasegawa, M.; Saigo, K. J. Org. Chem. 1993, 58, 579-857; Hashimoto, Y.; Sato, Y.; Takeshita, N.; Kudo, K.; Saigo, K. Tetrahedron 1994, 50, 8317-8336; Miyauchi, H.; Nakamura, T.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 1731-1737; Miyauchi, H.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 3591-3598; Liu, C.; Kudo, K.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1996, 61, 494-502; Liu, C.; Hashimoto, Y.; Saigo, K. Tetrahedron Lett. 1996, 37, 6177-6180; Gill, D. M.; Pegg, N. A.; Rayner, C. M. Tetrahedron 1996, 52, 3609-3630.
11. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions of epoxides: Kudo, K.; Saigo, K.; Hashimoto, Y.; Saito, K.; Hasegawa, M. Chem. Lett. 1992, 1449-1452; Kudo, K.; Hashimoto, Y.; Houchigai, H.; Hasegawa, M.; Saigo, K. Bull. Chem. Soc. Jpn. 1993, 66, 848-856; Kudo, K.; Hashimoto, Y.; Sukegawa, M.; Hasegawa, M.; Saigo, K. J. Org. Chem. 1993, 58, 579-857; Hashimoto, Y.; Sato, Y.; Takeshita, N.; Kudo, K.; Saigo, K. Tetrahedron 1994, 50, 8317-8336; Miyauchi, H.; Nakamura, T.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 1731-1737; Miyauchi, H.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 3591-3598; Liu, C.; Kudo, K.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1996, 61, 494-502; Liu, C.; Hashimoto, Y.; Saigo, K. Tetrahedron Lett. 1996, 37, 6177-6180; Gill, D. M.; Pegg, N. A.; Rayner, C. M. Tetrahedron 1996, 52, 3609-3630.
12. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions of epoxides: Kudo, K.; Saigo, K.; Hashimoto, Y.; Saito, K.; Hasegawa, M. Chem. Lett. 1992, 1449-1452; Kudo, K.; Hashimoto, Y.; Houchigai, H.; Hasegawa, M.; Saigo, K. Bull. Chem. Soc. Jpn. 1993, 66, 848-856; Kudo, K.; Hashimoto, Y.; Sukegawa, M.; Hasegawa, M.; Saigo, K. J. Org. Chem. 1993, 58, 579-857; Hashimoto, Y.; Sato, Y.; Takeshita, N.; Kudo, K.; Saigo, K. Tetrahedron 1994, 50, 8317-8336; Miyauchi, H.; Nakamura, T.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 1731-1737; Miyauchi, H.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 3591-3598; Liu, C.; Kudo, K.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1996, 61, 494-502; Liu, C.; Hashimoto, Y.; Saigo, K. Tetrahedron Lett. 1996, 37, 6177-6180; Gill, D. M.; Pegg, N. A.; Rayner, C. M. Tetrahedron 1996, 52, 3609-3630.
13. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions of epoxides: Kudo, K.; Saigo, K.; Hashimoto, Y.; Saito, K.; Hasegawa, M. Chem. Lett. 1992, 1449-1452; Kudo, K.; Hashimoto, Y.; Houchigai, H.; Hasegawa, M.; Saigo, K. Bull. Chem. Soc. Jpn. 1993, 66, 848-856; Kudo, K.; Hashimoto, Y.; Sukegawa, M.; Hasegawa, M.; Saigo, K. J. Org. Chem. 1993, 58, 579-857; Hashimoto, Y.; Sato, Y.; Takeshita, N.; Kudo, K.; Saigo, K. Tetrahedron 1994, 50, 8317-8336; Miyauchi, H.; Nakamura, T.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 1731-1737; Miyauchi, H.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 3591-3598; Liu, C.; Kudo, K.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1996, 61, 494-502; Liu, C.; Hashimoto, Y.; Saigo, K. Tetrahedron Lett. 1996, 37, 6177-6180; Gill, D. M.; Pegg, N. A.; Rayner, C. M. Tetrahedron 1996, 52, 3609-3630.
14. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions of epoxides: Kudo, K.; Saigo, K.; Hashimoto, Y.; Saito, K.; Hasegawa, M. Chem. Lett. 1992, 1449-1452; Kudo, K.; Hashimoto, Y.; Houchigai, H.; Hasegawa, M.; Saigo, K. Bull. Chem. Soc. Jpn. 1993, 66, 848-856; Kudo, K.; Hashimoto, Y.; Sukegawa, M.; Hasegawa, M.; Saigo, K. J. Org. Chem. 1993, 58, 579-857; Hashimoto, Y.; Sato, Y.; Takeshita, N.; Kudo, K.; Saigo, K. Tetrahedron 1994, 50, 8317-8336; Miyauchi, H.; Nakamura, T.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 1731-1737; Miyauchi, H.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 3591-3598; Liu, C.; Kudo, K.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1996, 61, 494-502; Liu, C.; Hashimoto, Y.; Saigo, K. Tetrahedron Lett. 1996, 37, 6177-6180; Gill, D. M.; Pegg, N. A.; Rayner, C. M. Tetrahedron 1996, 52, 3609-3630.
15. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions of epoxides: Kudo, K.; Saigo, K.; Hashimoto, Y.; Saito, K.; Hasegawa, M. Chem. Lett. 1992, 1449-1452; Kudo, K.; Hashimoto, Y.; Houchigai, H.; Hasegawa, M.; Saigo, K. Bull. Chem. Soc. Jpn. 1993, 66, 848-856; Kudo, K.; Hashimoto, Y.; Sukegawa, M.; Hasegawa, M.; Saigo, K. J. Org. Chem. 1993, 58, 579-857; Hashimoto, Y.; Sato, Y.; Takeshita, N.; Kudo, K.; Saigo, K. Tetrahedron 1994, 50, 8317-8336; Miyauchi, H.; Nakamura, T.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 1731-1737; Miyauchi, H.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 3591-3598; Liu, C.; Kudo, K.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1996, 61, 494-502; Liu, C.; Hashimoto, Y.; Saigo, K. Tetrahedron Lett. 1996, 37, 6177-6180; Gill, D. M.; Pegg, N. A.; Rayner, C. M. Tetrahedron 1996, 52, 3609-3630.
16. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions of epoxides: Kudo, K.; Saigo, K.; Hashimoto, Y.; Saito, K.; Hasegawa, M. Chem. Lett. 1992, 1449-1452; Kudo, K.; Hashimoto, Y.; Houchigai, H.; Hasegawa, M.; Saigo, K. Bull. Chem. Soc. Jpn. 1993, 66, 848-856; Kudo, K.; Hashimoto, Y.; Sukegawa, M.; Hasegawa, M.; Saigo, K. J. Org. Chem. 1993, 58, 579-857; Hashimoto, Y.; Sato, Y.; Takeshita, N.; Kudo, K.; Saigo, K. Tetrahedron 1994, 50, 8317-8336; Miyauchi, H.; Nakamura, T.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 1731-1737; Miyauchi, H.; Ohashi, N. Bull. Chem. Soc. Jpn. 1995, 68, 3591-3598; Liu, C.; Kudo, K.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1996, 61, 494-502; Liu, C.; Hashimoto, Y.; Saigo, K. Tetrahedron Lett. 1996, 37, 6177-6180; Gill, D. M.; Pegg, N. A.; Rayner, C. M. Tetrahedron 1996, 52, 3609-3630.
17. Liu, C.; Hashimoto, Y.; Kudo, K.; Saigo, K. Bull. Chem. Soc. Jpn. 1996, 69, 2095-2105.
18. 2.
19. These results will be published as a full paper in the future.
20. The stereochemistry of the products was confirmed by comparison with that of authentic samples.
21. Nakagawa, I.; Aki, K.; Hata, T. J. Chem. Soc., Perkin Trans. 1 1983, 1315-1318.