CsF in organic synthesis. Inversion of secondary mesylates and tosylates

Tetrahedron

Volumn 53, Issue 40, 1997, Pages 13633-13640

  Otera, Junzo ^a   Nakazawa, Koichi ^a   Sekoguchi, Koichi ^a   Orita, Akihiro ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030886371     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00900-9     Document Type: Article

References (40)

1. Mitsunobu, O. Synthesis 1981, 1. Hughes, D. L. Organic Reactions 1992, 42, 335.
2. Mitsunobu, O. Synthesis 1981, 1. Hughes, D. L. Organic Reactions 1992, 42, 335.
3. Moriarty, R. M.; Zhuang, H.; Penmastra, R.; Liu, K.; Awasthi, A. K.; Tuladhat, S. M.; Rao, M. S. C.; Singh, V. K. Tetrahedron Lett. 1993, 34, 8029. Effenberger, F.; Burkard, U.; Willfahrt, J. Angew. Chem. Int. Ed. Engl. 1983, 22, 65.
4. Moriarty, R. M.; Zhuang, H.; Penmastra, R.; Liu, K.; Awasthi, A. K.; Tuladhat, S. M.; Rao, M. S. C.; Singh, V. K. Tetrahedron Lett. 1993, 34, 8029. Effenberger, F.; Burkard, U.; Willfahrt, J. Angew. Chem. Int. Ed. Engl. 1983, 22, 65.
5. Boivin, J.; Henriet, E.; Zard, S. Z. J. Am. Chem. Soc. 1994, 116, 9739.
6. Barrett, A. G.; Koike, N.; Procopiou, P. A. J. Chem. Soc., Chem. Commun. 1995, 1403.
7. Corey, E. J.; Nicolaou, K. C.; Shibasaki, M.; Machida, Y.; Shiner, C. S. Tetrahedron Lett. 1975, 3183.
8. Radüchel, B. Synthesis 1980, 292.
9. Cainelli, G.; Manescalchi, F.; Martell, G.; Panunzio, M.; Plessi, L. Tetrahedron Lett. 1985, 26, 3369.
10. Kruizinga, W. H.; Strijtveen, B.; Kellog, R. M. J. Org. Chem. 1981, 46, 4321. Huffman, J. W.; Desai, R. C. Synth. Commun. 1983, 13, 553. Lerchen, H.-G.; Kunz, H. Tetrahedron Lett. 1985, 26, 5257. Burkard, U.; Effenberger, F. Chem. Ber. 1986, 119, 1594.
11. Kruizinga, W. H.; Strijtveen, B.; Kellog, R. M. J. Org. Chem. 1981, 46, 4321. Huffman, J. W.; Desai, R. C. Synth. Commun. 1983, 13, 553. Lerchen, H.-G.; Kunz, H. Tetrahedron Lett. 1985, 26, 5257. Burkard, U.; Effenberger, F. Chem. Ber. 1986, 119, 1594.
12. Kruizinga, W. H.; Strijtveen, B.; Kellog, R. M. J. Org. Chem. 1981, 46, 4321. Huffman, J. W.; Desai, R. C. Synth. Commun. 1983, 13, 553. Lerchen, H.-G.; Kunz, H. Tetrahedron Lett. 1985, 26, 5257. Burkard, U.; Effenberger, F. Chem. Ber. 1986, 119, 1594.
13. Kruizinga, W. H.; Strijtveen, B.; Kellog, R. M. J. Org. Chem. 1981, 46, 4321. Huffman, J. W.; Desai, R. C. Synth. Commun. 1983, 13, 553. Lerchen, H.-G.; Kunz, H. Tetrahedron Lett. 1985, 26, 5257. Burkard, U.; Effenberger, F. Chem. Ber. 1986, 119, 1594.
14. Torisawas, Y.; Okabe, H.; Ikegami, S. Chem. Lett. 1984, 1555.
15. Sato, K.; Yoshitomo, A. Chem. Lett. 1995, 39.
16. Shimizu, T.; Hiranuma, S.; Nakata, T. Tetrahedron Lett. 1996, 37, 6145.
17. Strijtveen, B.; Kellog, R. M. J. Org. Chem. 1986, 51, 3664. Hof, R. P.; Kellog, R. M. J. Chem. Soc. Perkin Trans. 1 1995, 1247.
18. Strijtveen, B.; Kellog, R. M. J. Org. Chem. 1986, 51, 3664. Hof, R. P.; Kellog, R. M. J. Chem. Soc. Perkin Trans. 1 1995, 1247.
19. Sato, T.; Otera, J. Synlett 1995, 336.
20. Sato, T.; Otera, J. J. Org. Chem. 1995, 60, 2627.
21. 3CN) yields under the same reaction conditions employed in entry 1 in Table 1. For the similar solvent effect in CsF-promoted alkylation of carboxylic acids, see: Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1992, 57, 2166.
22. Clark, J. H.; Emsley, J. J. Chem. Soc. Dalton 1975, 2129. Clark, J. H.; Holland, H. L.; Miller, J. M. Tetrahedron Lett. 1976, 3361. Clark, J. H.; Miller, J. M. J. Am. Chem. Soc. 1977, 99, 498.
23. Clark, J. H.; Emsley, J. J. Chem. Soc. Dalton 1975, 2129. Clark, J. H.; Holland, H. L.; Miller, J. M. Tetrahedron Lett. 1976, 3361. Clark, J. H.; Miller, J. M. J. Am. Chem. Soc. 1977, 99, 498.
24. Clark, J. H.; Emsley, J. J. Chem. Soc. Dalton 1975, 2129. Clark, J. H.; Holland, H. L.; Miller, J. M. Tetrahedron Lett. 1976, 3361. Clark, J. H.; Miller, J. M. J. Am. Chem. Soc. 1977, 99, 498.
25. Shoda, S.; Mukaiyama, T. Chem. Lett. 1980, 391.
26. Noyce, D. S.; Johnston, B. E.; Weinstein, B. J. Org. Chem. 1969, 34, 463.
27. Kenyon, J.; Phillips, H.; Turley, H. G. J. Chem. Soc. 1925, 127, 399.
28. Garcia, J.; Vilarrasa, J.; Bordas, X.; Banaszek, A. Tetrahedron Lett. 1986, 27, 639.
29. Humphrey, G. R.; DeMarco, A. M.; Methre, D. J.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 588.
30. Kamal, A.; Ramalingam, T.; Venugopal, N. Tetrahedron: Asymmetry 1991, 2, 39.
31. Amos, R. A.; Emblidge, E. W.; Havens, N. J. Org. Chem. 1983, 48, 3598.
32. Hojo, K.; Yoshino, H.; Mukaiyama, T. Chem. Lett. 1977, 133.
33. Mitsunobu, O,; Wada, M.; Sano, T. J. Am. Chem. Soc. 1972, 94, 679.
34. Hojo, K.; Kobayashi, S.; Soai, K.; Ikeda, S.; Mukaiyama, T. Chem. Lett. 1977, 635.
35. Tanigawa, Y.; Kanamaru, H.; Murahashi, S.-I. Tetrahedron Lett. 1975, 4655.
36. Saito, S.; Yokoyama, H.; Ishikawa, T.; Niwa, N.; Moriwake, T. Tetrahedron Lett. 1991, 32, 663.
37. Bischoff, C. A. Chem. Ber. 1880, 13, 2161.
38. Kurihara, T.; Sugizaki, M.; Kime, I.; Wada, M.; Mitsunobu, O. Bull. Chem. Soc. Jpn. 1981, 54, 2107.
39. Krafft, G. A.; Sidall, L. Tetrahedron Lett. 1985, 26, 4867.
40. Herbert, E.; Mazaleyrat, J.; Welvart, Z. J. Chem. Soc., Chem. Commun. 1977, 877.