New methods for carbon-nitrogen, carbon-sulfur, and carbon-carbon bond formations by quinone-mediated oxidation-reduction condensation using alkyl diphenylphosphinites

Proceedings of the Japan Academy Series B: Physical and Biological Sciences

Volumn 81, Issue 4, 2005, Pages 103-109

  Mukaiyama, Teruaki ^a,b   Ikegai, Kazuhiro ^a,b   Aoki, Hidenori ^a,b   Pluempanupat, Wanchai ^a,b   Masutani, Kouta ^a,b  

^a KITASATO INSTITUTE   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

1,4 benzoquinone; Alkyl diphenylphosphinite; Bimolecular nucleophilic substitution; Dehydration; Inversion of stereochemistry; Oxidation reduction condensation

Indexed keywords

EID: 21044437117     PISSN: 03862208     EISSN: None     Source Type: Journal    
DOI: 10.2183/pjab.81.103     Document Type: Article

References (29)

1. Mukaiyama, T., Kuwajima, I., and Suzuki, Z. (1963) J. Org. Chem. 28, 2024-2027.
2. Kuwajima, I., and Mukaiyama, T. (1964) J. Org. Chem. 29, 1385-1386.
3. Mukaiyama, T., Mutsueda, R., and Suzuki, M. (1970) Tetrahedron Lett. 11, 1901-1904.
4. Corey, E. J., Nicolaou, K. C., and Melvin, L. S. (1975) J. Am. Chem. Soc. 97, 653-654.
5. Corey, E. J., and Nicolaou, K. C. (1974) J. Am. Chem. Soc. 96, 5614-5616;
6. Corey, E. J., Brunelle, D. J., and Stork, P. J. (1976) Tetrahedron Lett. 17, 3405-3408.
7. Corey, E. J., Nicolaou, K. C., and Melvin, L. S. (1975) J. Am. Chem. Soc. 97, 654-655.
8. Corey, E. J., Ulrich, P., and Fitzpatrick, J. M. (1976) J. Am. Chem. Soc. 98, 222-224.
9. Corey, E. J., Nicolaou, K. C., and Toru, T. (1975) J. Am. Chem. Soc. 97, 2287-2288.
10. Corey, E. J., and Bhattacharyya, S. (1977) Tetrahedron Lett. 18, 3919-3922.
11. Bundy, G. L., Peterson, D. C., Cornette, J. C., Miller, W. L., Spilman, C. H., and Wilks, J. W. (1983) J. Med. Chem. 26, 1089-1099.
12. Mitsunobu, O., Yamada, M., and Mukaiyama, T. (1967) Bull. Chem. Soc. Jpn. 40, 935-939.
13. Mitsunobu, O. (1981) Synthesis 1981, 1-28;
14. Hughes, D. L. (1993) The Mitsunobu reaction. Organic Reactions, vol. 42, John Wiley & Sons, New York, pp. 335-656;
15. Hughes, D. L. (1996) Org. Prep. Proced. Int. 28, 127-164.
16. Sakamoto, I., Kaku, H., and Tsunoda, T. (2003) Chem. Pharm. Bull. 51, 474-476;
17. Itô, S., and Tsunoda, T. (1999) Pure Appl. Chem. 71, 1053-1057.
18. Shintou, T., Fukumoto, K., and Mukaiyama, T. (2004) Bull. Chem. Soc. Jpn. 77, 1569-1579;
19. Shintou, T., Kikuchi, W., and Mukaiyama, T. (2003) Bull. Chem. Soc. Jpn. 76, 1645-1667;
20. Shintou, T., and Mukaiyama, T. (2004) J. Am. Chem. Soc. 126, 7359-7367.
21. Mukaiyama, T., and Aoki, H. (2005) Chem. Lett. 34, 142-143.
22. Tsunoda, T., Ozaki, F., and Itô, S. (1994) Tetrahedron Lett. 35, 5081-5082.
23. Lai, J.-Y., Yu, J., Hawkins, R. D., and Falck, J. R. (1995) Tetrahedron Lett. 36, 5691-5694;
24. Tsunoda, T., Nagaku, M., Nagino, C., Kawamura, Y., Ozaki, F., Hioki, H., and Itô, S. (1995) Tetrahedron Lett. 36, 2531-2534.
25. Misun, M., and Pfaltz, A. (1996) Helv. Chim. Acta 79, 961-972.
26. Ikegai, K., and Mukaiyama, T. (2005) Chem. Lett. 34, 638-639.
27. Mukaiyama, T., and Ikegai, K. (2004) Chem. Lett. 33, 1522-1523.
28. Stratmann, O., Kaiser, B., Fröhlich, R., Meyer, O., and Hoppe, D. (2001) Chem. Eur. J. 7, 423-435.
29. Ramirez, F., and Dershowitz, S. (1956) J. Am. Chem. Soc. 78, 5614-5622.