An efficient approach towards the stereospecific synthesis of epoxides from phospholene oxides

Tetrahedron Letters

Volumn 44, Issue 11, 2003, Pages 2339-2341

  Yamashita, Mitsuji ^a   Reddy, Valluru Krishna ^a   Rao, Lakonda Nagaprasada ^a   Haritha, Buchammagari ^a   Maeda, Motoki ^a   Suzuki, Keiji ^a   Totsuka, Hirono ^a   Takahashi, Masaki ^a   Oshikawa, Tatsuo ^b  

^a SHIZUOKA UNIVERSITY   (Japan)

^b NUMAZU COLLEGE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; OXIDE; PEROXIDE; SODIUM PEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; EPOXIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOSPECIFICITY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0037430584     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00255-7     Document Type: Article

References (15)

1. For a recent review on epoxide chemistry and reactivity, see: Taylor S.K. Tetrahedron. 56:2000;1149-1163. and references cited therein.
2. Mitsuya H., Weinhold K.J., Furman P.A., St. Clair M.H., Lehrmann S.N., Gallo R.S., Bolognes D., Barry D.W., Broder S. Proc. Natl. Acad. Sci. USA. 82:1985;7096-7100.
3. Secrist J.A. III, Riggs R.M., Tiwari K.N., Montgomery J.A. J. Med. Chem. 35:1992;533-538.
4. Shealy Y.F., Clayton J.D. J. Am. Chem. Soc. 88:1966;3885-3887.
5. McCormack J.B., Getchell J.P., Mitchel S.W., Hicks D.R. Lancet ii. 1984;1367-1369.
6. Quin L.D., Symmes C., Middlemas E.D. Jr., Lawson H.F. J. Org. Chem. 45:1980;4688-4694.
7. Yamashita M., Suzuki K., Iida A., Ikai K., Reddy P.M., Oshikawa T. J. Carbohydr. Chem. 18:1999;915-935.
8. Epoxidation on phospholene oxides using a mixture of hydrogen peroxide and various catalysts is currently under way in our laboratory and the results will be published elsewhere.
9. Monitoring the progression of the reactions by TLC showed that the reactions were proceeding very slowly at below 30°C.
10. For example, see: Yamashita M., Uchimura M., Iida A., Parkayani L., Clardy J. J. Chem. Soc., Chem. Commun. 1988;569-570.
11. -1, radiation CuKα (λ=1.54178 Å), T=23.0°C, no. observations=(I>3.00σ(I)), 1218, no. of variables=163, reflection/parameter ratio=7.47, R, Rw, 0.063, 0.068. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC 201197. Copies may be requested free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
12. Phospholene oxides 1a-g were prepared from the reported synthetic methods, see: Krishna Reddy V., Onogawa J.I., Rao L.N., Oshikawa T., Takahashi M., Yamashita M. J. Heterocyclic Chem. 39:2002;69-75.
13. 4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel using 20:1:1 EtOAc, n-hexane and methanol as the eluent, to give product 2a as a colorless solid. Mp: 113-115°C.
14. 3 complex: δ 9.85-8.22 (3br s, 4H, Ph), 5.01 (d, 1H, J=25.7 Hz, H-2), 4.00 (br s, 1H, H-3), 2.86-2.20 (m, 4H, H-4,5).
15. 31P NMR (90 MHz), mass, and IR spectral analyses. The stereochemistry of other products 2b-e was assigned by chemical shift reagent studies, crystallographic analogy of compound 2a and also based on other similar compounds reported in the literature: see, Ref. 6.