Stereoelectronic effect on stereoselective olefination of ketones providing tetrasubstituted olefins via ynolates

Journal of Organic Chemistry

Volumn 65, Issue 17, 2000, Pages 5443-5445

  Shindo, Mitsuru ^a   Sato, Yusuke ^a   Shishido, Kozo ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CARBONYL DERIVATIVE; KETONE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034714411     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000650l     Document Type: Article

References (35)

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19. Vieregge, H.; Bos, H. J. T.; Arens, J. F. Recl. Trav. Chim Pays-Bas 1959, 78, 664-666. Vieregge, H.; Schmidt, H. M.; Renema, J.; Bos, H. J. T.; Arens, J. F. Recl. Trav. Chim Pays-Bas 1966, 85, 929-951. Bos, H. J. T.; Boleij, J. Recl. Trav. Chim Pays-Bas 1969, 88, 465-473. Pornet, J.; Khouz, B.; Miginiac, L. Tetrahedron Lett. 1985, 26, 1861-1862. Pornet, J.; Rayadh, A.; Miginiac, L. Tetrahedron Lett. 1986, 27, 5479-5482. Zakarya, D.; Rayadh, A.; Samih, M: Lakhlifi, T. Tetrahedron Lett. 1994, 35, 405-408. Zakarya, D.; Rayadh, A.; Samih, M.; Lakhlifi, T. Tetrahedron Lett. 1994, 35, 2345-2348. Crich, D.; Crich, J. Z., Tetrahedron Lett. 1994, 35, 2469-2472.
20. Vieregge, H.; Bos, H. J. T.; Arens, J. F. Recl. Trav. Chim Pays-Bas 1959, 78, 664-666. Vieregge, H.; Schmidt, H. M.; Renema, J.; Bos, H. J. T.; Arens, J. F. Recl. Trav. Chim Pays-Bas 1966, 85, 929-951. Bos, H. J. T.; Boleij, J. Recl. Trav. Chim Pays-Bas 1969, 88, 465-473. Pornet, J.; Khouz, B.; Miginiac, L. Tetrahedron Lett. 1985, 26, 1861-1862. Pornet, J.; Rayadh, A.; Miginiac, L. Tetrahedron Lett. 1986, 27, 5479-5482. Zakarya, D.; Rayadh, A.; Samih, M: Lakhlifi, T. Tetrahedron Lett. 1994, 35, 405-408. Zakarya, D.; Rayadh, A.; Samih, M.; Lakhlifi, T. Tetrahedron Lett. 1994, 35, 2345-2348. Crich, D.; Crich, J. Z., Tetrahedron Lett. 1994, 35, 2469-2472.
21. Vieregge, H.; Bos, H. J. T.; Arens, J. F. Recl. Trav. Chim Pays-Bas 1959, 78, 664-666. Vieregge, H.; Schmidt, H. M.; Renema, J.; Bos, H. J. T.; Arens, J. F. Recl. Trav. Chim Pays-Bas 1966, 85, 929-951. Bos, H. J. T.; Boleij, J. Recl. Trav. Chim Pays-Bas 1969, 88, 465-473. Pornet, J.; Khouz, B.; Miginiac, L. Tetrahedron Lett. 1985, 26, 1861-1862. Pornet, J.; Rayadh, A.; Miginiac, L. Tetrahedron Lett. 1986, 27, 5479-5482. Zakarya, D.; Rayadh, A.; Samih, M: Lakhlifi, T. Tetrahedron Lett. 1994, 35, 405-408. Zakarya, D.; Rayadh, A.; Samih, M.; Lakhlifi, T. Tetrahedron Lett. 1994, 35, 2345-2348. Crich, D.; Crich, J. Z., Tetrahedron Lett. 1994, 35, 2469-2472.
22. Vieregge, H.; Bos, H. J. T.; Arens, J. F. Recl. Trav. Chim Pays-Bas 1959, 78, 664-666. Vieregge, H.; Schmidt, H. M.; Renema, J.; Bos, H. J. T.; Arens, J. F. Recl. Trav. Chim Pays-Bas 1966, 85, 929-951. Bos, H. J. T.; Boleij, J. Recl. Trav. Chim Pays-Bas 1969, 88, 465-473. Pornet, J.; Khouz, B.; Miginiac, L. Tetrahedron Lett. 1985, 26, 1861-1862. Pornet, J.; Rayadh, A.; Miginiac, L. Tetrahedron Lett. 1986, 27, 5479-5482. Zakarya, D.; Rayadh, A.; Samih, M: Lakhlifi, T. Tetrahedron Lett. 1994, 35, 405-408. Zakarya, D.; Rayadh, A.; Samih, M.; Lakhlifi, T. Tetrahedron Lett. 1994, 35, 2345-2348. Crich, D.; Crich, J. Z., Tetrahedron Lett. 1994, 35, 2469-2472.
23. Vieregge, H.; Bos, H. J. T.; Arens, J. F. Recl. Trav. Chim Pays-Bas 1959, 78, 664-666. Vieregge, H.; Schmidt, H. M.; Renema, J.; Bos, H. J. T.; Arens, J. F. Recl. Trav. Chim Pays-Bas 1966, 85, 929-951. Bos, H. J. T.; Boleij, J. Recl. Trav. Chim Pays-Bas 1969, 88, 465-473. Pornet, J.; Khouz, B.; Miginiac, L. Tetrahedron Lett. 1985, 26, 1861-1862. Pornet, J.; Rayadh, A.; Miginiac, L. Tetrahedron Lett. 1986, 27, 5479-5482. Zakarya, D.; Rayadh, A.; Samih, M: Lakhlifi, T. Tetrahedron Lett. 1994, 35, 405-408. Zakarya, D.; Rayadh, A.; Samih, M.; Lakhlifi, T. Tetrahedron Lett. 1994, 35, 2345-2348. Crich, D.; Crich, J. Z., Tetrahedron Lett. 1994, 35, 2469-2472.
24. Vieregge, H.; Bos, H. J. T.; Arens, J. F. Recl. Trav. Chim Pays-Bas 1959, 78, 664-666. Vieregge, H.; Schmidt, H. M.; Renema, J.; Bos, H. J. T.; Arens, J. F. Recl. Trav. Chim Pays-Bas 1966, 85, 929-951. Bos, H. J. T.; Boleij, J. Recl. Trav. Chim Pays-Bas 1969, 88, 465-473. Pornet, J.; Khouz, B.; Miginiac, L. Tetrahedron Lett. 1985, 26, 1861-1862. Pornet, J.; Rayadh, A.; Miginiac, L. Tetrahedron Lett. 1986, 27, 5479-5482. Zakarya, D.; Rayadh, A.; Samih, M: Lakhlifi, T. Tetrahedron Lett. 1994, 35, 405-408. Zakarya, D.; Rayadh, A.; Samih, M.; Lakhlifi, T. Tetrahedron Lett. 1994, 35, 2345-2348. Crich, D.; Crich, J. Z., Tetrahedron Lett. 1994, 35, 2469-2472.
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30. The conversion of the β-lactone enolate into an olefin via "forbidden" β-elimination has been reported by Mulzer. This mechanism cannot be ruled out: see ref 7c.
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34. Kirmse, W.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1984, 106, 7989-7991. Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 2099-2111. Spellmeyer, D. C.; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 3412-3416. Kallel, E. A.; Wang, Y.; Spellmeyer, D. C.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 6759-6763. Li, Y.; Rubin, Y.; Diederich, F.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 1618-1623.
35. Kirmse, W.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1984, 106, 7989-7991. Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 2099-2111. Spellmeyer, D. C.; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 3412-3416. Kallel, E. A.; Wang, Y.; Spellmeyer, D. C.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 6759-6763. Li, Y.; Rubin, Y.; Diederich, F.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 1618-1623.