Hexacoordinate phosphates bearing an oxaphosphetane ring: Characterization and stereomutation

Tetrahedron Letters

Volumn 38, Issue 4, 1997, Pages 547-550

  Kojima, Satoshi ^a   Akiba, Kin Ya ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHORANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0031031932     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02368-4     Document Type: Article

References (24)

1. For leading preferences see: (a) Wadsworth, W. S., Jr. Org. React. 1977, 25, 73-253.
2. (b) Cadogan, J. I. G. Organophosphorus Reagents in Organic Synthesis; Academic Press: New York, 1979.
3. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
4. (d) Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, p 730-817.
5. (e) Johnson, A. W.; Ylides and Imines of Phosphorus; Wiley-Interscience: New York, 1993.
6. (f) Vedejs, E.; Peterson, M. J. Top. Stereochem. 1994, 21, 1-157.
7. (g) Clayden, J.; Warren, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 241-270.
8. Kojima, S; Takagi, R.; Akiba K.-y. submitted for publication.
9. Bojin, M. L.; Barkallah, S.; Evans, S. A., Jr. J. Am. Chem. Soc. 1996, 118, 1551-1552.
10. For recent leading preferences see: (a) Cherkasoz, R. A.; Ploezhaeva Ups. Khim. 1987, 56, 287-321.
11. (b) Burgada, R; Setton, R. In The Chemistry of Organophosphorus Compounds, Hartley, F. R., Ed.; Wiley-Interscience: Chichester, 1994.
12. Yamamoto, Y.; Fujikawa, H.; Fujishima, H.; Akiba, K.-y. J. Am. Chem. Soc. 1989, 111, 2276-2283.
13. Yamamoto, Y.; Ohdoi, K.; Chen, X.; Kitano, M.; Akiba, K.-y. Organometallics 1993, 12, 1857-1864.
14. The T. Kawashima-R. Okazaki group of the University of Tokyo has carried out an independent study on the same kind of hexacoordinate phosphorus compounds. They have also reported the synthesis of phosphoranes bearing oxaphosphetane rings having α electron-withdrawing groups. Kawashima, T.; Kato, K.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 869-870.
15. (a) Granoth, I.; Martin, J. C. J. Am. Chem. Soc. 1979, 101, 4623-4626.
16. (b) Kojima, S.; Kajiyama, K.; Akiba, K.-y. Tetrahedron Lett. 1994, 55, 7037-7040.
17. (c) Kojima, S.; Kajiyama, K.; Akiba, K.-y. Bull. Chem. Soc. Jpn. 1995, 68, 1785-1797.
18. (d) Kojima, S.; Nakamoto, M.; Kajiyama, K.; Akiba, K.-y. Tetrahedron Lett. 1995, 36, 22612264.
19. 3P: C, 53.95; H, 2.97. Found: C, 53.74; H, 2.69.
20. The other two correspond to (1) an isomer having one Martin ligand oxygen trans to the oxaphosphetane oxygen, and the other Martin ligand oxygen trans to a Martin ligand carbon; (2) an isomer having all the oxygens trans to carbons.
21. 3CN) -121.8.
22. 3)-22.1.
23. Cavezzan, J.; Etemad-Moghadam, G. Koenig, M; Klaebe, A. Tetrahedron Lett. 1979, 9, 795-798.
24. Font Freide, J. J. H. M.; Trippett, S. J. Chem. Soc., Chem. Commun. 1980, 934-936.