First synthesis of optically pure selenuranes and stereoselective alkaline hydrolysis. Their application to asymmetric [2,3] sigmatropic rearrangement of allylic selenoxides

Tetrahedron

Volumn 53, Issue 36, 1997, Pages 12115-12129

  Kurose, Noriyuki ^a   Takahashi, Tamiko ^a   Koizumi, Toru ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; ORGANOSELENIUM DERIVATIVE;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; CRYSTALLOGRAPHY; DRUG SYNTHESIS; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0030874729     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00546-2     Document Type: Article

References (27)

1. For recent reviews, see: (a) Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986.
2. (b) Back, T. G. The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1987; Vol. 2.
3. For some examples, see: (c) McCullough, J. D.; Hamburgar, G. J. Am. Chem. Soc. 1941, 63, 803; 1942, 64, 508.
4. For some examples, see: (c) McCullough, J. D.; Hamburgar, G. J. Am. Chem. Soc. 1941, 63, 803; 1942, 64, 508.
5. (d) Lindgren, B. Acta Chem. Scand. 1972, 47, 3289.
6. (e) Reich, H. J. C. J. Am. Chem. Soc. 1973, 95, 964.
7. (f) Fujihara, H.; Mima, H.; Ikemori, M.; Furukawa, N. Ibid. 1991, 113, 6337.
8. (g) Fujihara, H.; Saito, R.; Yabe, M.; Furukawa, N. Chem. Lett. 1992, 1437.
9. (h) Fujihara, H.; Mima, H.; Erata, T.; Furukawa, N. J. Am. Chem. Soc. 1992, 114, 3117.
10. (i) Fujihara, H.; Mima, H.; Erata, T.; Furukawa, N. Ibid. 1993, 115, 9826.
11. (j) Kawashima, T.; Ohno, F.; Okazaki, R. Ibid. 1993, 115, 10434.
12. (k) Fujihara, H.; Mima, H.; Furukawa, N. Tetrahedron 1996, 52, 13951.
13. Takahashi, T.; Kurose, N.; Kawanami, S.; Arai, Y.; Koizumi, T.; Shiro, M. J. Org. Chem. 1994, 59, 3262.
14. Poth, N. Rev. Tech. Luxemb. 1976, 68, 195; Chem. Abstr. 1977, 87, 135965k.
15. Poth, N. Rev. Tech. Luxemb. 1976, 68, 195; Chem. Abstr. 1977, 87, 135965k.
16. Scaborough, R. M., Jr.; Toder, B. H.; Smith, A. B., III. J. Am. Chem. Soc. 1980, 102, 3904.
17. Kurose, N.; Takahashi, T.; Koizumi, T. J. Org. Chem. 1996, 61, 2932.
18. Designation of absolute configuration at tetracoordinate selenium(IV) was followed by an extension of the Cahn, Ingold, Prelog (CIP) R-S nomenclature proposed by Martin, J. C. and Balthazor, T. M. J. Am. Chem. Soc. 1977, 99, 152.
19. Reich, H. J.; Yelm, K. E. J. Org. Chem. 1991, 56, 5672.
20. Davis, F. A.; Reddy, T. J. Org. Chem. 1992, 57, 2599.
21. (a) Komatsu, K.; Nishibayashi, Y.; Uemura, S. Tetrahedron Lett. 1993, 34, 2339.
22. (b) Nishibayashi, Y.; Singh, J.; Fukuzawa, S.; Uemura, S. J. Org. Chem. 1995, 60, 4114.
23. Aristoff, P. A.; Johnson, P. D.; Harrison, A. W. J. Am. Chem. Soc. 1985, 107, 7967.
24. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
25. Ohloff, G.; Klein, E. Tetrahedron 1962, 18, 37.
26. 3) (R-form)} (ca. 30% ee).
27. Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1979, 18, 563.