Crystallization-induced asymmetric transformation of a tertiary phosphine

Journal of Organic Chemistry

Volumn 65, Issue 8, 2000, Pages 2337-2343

  Vedejs, Edwin ^a,b   Donde, Yariv ^b  

^a UNIVERSITY OF MICHIGAN   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IODINE; LITHIUM; METHYL IODIDE; N (2 FLUORENYL)ACETAMIDE; PHOSPHINE DERIVATIVE; SOLVENT;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CRYSTAL; CRYSTALLIZATION; DIASTEREOISOMER; EVAPORATION; TEMPERATURE;

EID: 0034697151     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991493x     Document Type: Article

References (32)

1. Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293.
2. (a) Vedejs, Edwin; Fields, Stephen C.; Schrimpf, Michael R. J. Am. Chem. Soc. 1993, 115, 11612.
3. (b) Vedejs, E.; Fields, S. C.; Hayashi, R.; Hitchcock, S. R.; Powell, D. R.; Schrimpf, M. R. J. Am. Chem. Soc. 1997, 119, 9293.
4. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates, and Resolutions; Krieger Publishing: Malabar, FL, 1994; Chapter 6. Secor, R. M. Chem. Rev. 1963, 63, 297.
5. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates, and Resolutions; Krieger Publishing: Malabar, FL, 1994; Chapter 6. Secor, R. M. Chem. Rev. 1963, 63, 297.
6. Organometal examples: Pope, W. J.; Peachey, S. J. J. Chem. Soc. Proc. 1900, 16, 42. Werner, A. Chem. Ber. 1912, 45, 3061.
7. Organometal examples: Pope, W. J.; Peachey, S. J. J. Chem. Soc. Proc. 1900, 16, 42. Werner, A. Chem. Ber. 1912, 45, 3061.
8. Carbohydrate examples: Hudson, C. S.; Dale, J. K J. Am. Chem. Soc. 1917, 39, 320. Hudson, C. S.; Yanovsky, E. J. Am. Chem. Soc. 1917, 39, 1013.
9. Carbohydrate examples: Hudson, C. S.; Dale, J. K J. Am. Chem. Soc. 1917, 39, 320. Hudson, C. S.; Yanovsky, E. J. Am. Chem. Soc. 1917, 39, 1013.
10. Mills, W. H.; Bain, A. M. J. Chem. Soc. 1910, 97, 1866. Leuchs, H.; Wutke, J. Chem. Ber. 1913, 46, 2420.
11. Mills, W. H.; Bain, A. M. J. Chem. Soc. 1910, 97, 1866. Leuchs, H.; Wutke, J. Chem. Ber. 1913, 46, 2420.
12. Mioskowski, C.; Solladié, G. Tetrahedron 1980, 36, 227. Reider, P. J.; Davis, P.; Hughes, D. L.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 955. Ihara, M.; Takahashi, M.; Taniguchi, N.; Yasui, K.; Fukumoto, K.; Kametani, K. J. Chem. Soc., Perkin Trans. 1 1989, 897. Reid, J. G.; Debiak-Krook, T. Tetrahedron Lett. 1990, 31, 3669. Wilen, S. H.; Qi, J. Z.; Williard, P. G. J. Org. Chem. 1991, 56, 485.
13. Mioskowski, C.; Solladié, G. Tetrahedron 1980, 36, 227. Reider, P. J.; Davis, P.; Hughes, D. L.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 955. Ihara, M.; Takahashi, M.; Taniguchi, N.; Yasui, K.; Fukumoto, K.; Kametani, K. J. Chem. Soc., Perkin Trans. 1 1989, 897. Reid, J. G.; Debiak-Krook, T. Tetrahedron Lett. 1990, 31, 3669. Wilen, S. H.; Qi, J. Z.; Williard, P. G. J. Org. Chem. 1991, 56, 485.
14. Mioskowski, C.; Solladié, G. Tetrahedron 1980, 36, 227. Reider, P. J.; Davis, P.; Hughes, D. L.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 955. Ihara, M.; Takahashi, M.; Taniguchi, N.; Yasui, K.; Fukumoto, K.; Kametani, K. J. Chem. Soc., Perkin Trans. 1 1989, 897. Reid, J. G.; Debiak-Krook, T. Tetrahedron Lett. 1990, 31, 3669. Wilen, S. H.; Qi, J. Z.; Williard, P. G. J. Org. Chem. 1991, 56, 485.
15. Mioskowski, C.; Solladié, G. Tetrahedron 1980, 36, 227. Reider, P. J.; Davis, P.; Hughes, D. L.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 955. Ihara, M.; Takahashi, M.; Taniguchi, N.; Yasui, K.; Fukumoto, K.; Kametani, K. J. Chem. Soc., Perkin Trans. 1 1989, 897. Reid, J. G.; Debiak-Krook, T. Tetrahedron Lett. 1990, 31, 3669. Wilen, S. H.; Qi, J. Z.; Williard, P. G. J. Org. Chem. 1991, 56, 485.
16. Mioskowski, C.; Solladié, G. Tetrahedron 1980, 36, 227. Reider, P. J.; Davis, P.; Hughes, D. L.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 955. Ihara, M.; Takahashi, M.; Taniguchi, N.; Yasui, K.; Fukumoto, K.; Kametani, K. J. Chem. Soc., Perkin Trans. 1 1989, 897. Reid, J. G.; Debiak-Krook, T. Tetrahedron Lett. 1990, 31, 3669. Wilen, S. H.; Qi, J. Z.; Williard, P. G. J. Org. Chem. 1991, 56, 485.
17. Noyori, R.; Uchiyama, M.; Nobori, T.; Hirose, M.; Hayakawa, Y. Aust. J. Chem. 1992, 45, 205.
18. Bader, A.; P., M.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1994, 1405. Bader, A.; Pabel, M.; Willis, A. C.; Wild, S. B. Inorg. Chem. 1996, 35, 3874.
19. Bader, A.; P., M.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1994, 1405. Bader, A.; Pabel, M.; Willis, A. C.; Wild, S. B. Inorg. Chem. 1996, 35, 3874.
20. Baechler, R. D.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 3090.
21. Naumann, K.; Zon, G.; Mislow, K. J. Am. Chem. Soc. 1969, 91, 7012.
22. Boese, R.; Haegele, G.; Kueckelhaus, W.; Seega, J.; Tossing, G. Chem.-Ztg. 1985, 109, 233-8.
23. (a) Smith, J. G.; Wright, G. F. J. Org. Chem. 1952, 17, 1116.
24. (b) Glaze, W. H.; Selman, C. M. J. Org. Chem. 1968, 33, 1987-90.
25. Tanaka, M.; Ogata, I. Bull. Chem. Soc. Jpn. 1975, 48, 1094.
26. Imamoto, T.; Oshiki,.; Onozawa, T.; Kusumoto,.T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244-52.
27. Imamoto, T.; Oshiki,. T.; Onozawa, T.; Matsuo, M.; Hikosaka,. T.; Yanagawa, M. Heteroat. Chem. 1992, 3, 563-75.
28. (a) Valentine, D. Jr.; Blount, J. F.; Toth, K. J. Org. Chem. 1980, 45, 3691.
29. (b) Fisher, C.; Mosher, H. S. Tetrahedron Lett. 1977, 18, 2487.
30. 3 acts as a positive chlorine source.
31. Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075.
32. Ebert, G. W.; Rieke, R. D. J. Org. Chem. 1988, 53, 4282-8.