Asymmetric Bayer-Villiger oxidation of cyclobutanones

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7583-7586

  Lopp, Margus ^a   Paju, Anne ^a   Kanger, T̃onis ^a   Pehk, Tõnis ^b  

^a TALLINN UNIVERSITY OF TECHNOLOGY   (Estonia)

^b NATIONAL INSTITUTE OF CHEMICAL PHYSICS AND BIOPHYSICS   (Estonia)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030583525     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01666-8     Document Type: Article

References (25)

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3. Mazzini, C., Lebreton, J., Furstoss, R. J.Org.Chem., 1996, 61, pp. 8-9; Kaneda, K., Ueno, S., Imanaka, T., Nishiyama, Y., Ishii, Y. J.Org.Chem,, 1994, 59, p. 2915.
4. 3. Alphand, V., Furstoss, R., In Enzyme Catalysis in Organic Synthesis; Drauz.K., Waldmann, H., Eds.; VCH Publishers: New York, 1995; pp 745-772; and references therein.
5. 4. Gusso, A., Baccin, C., Pinna, F., Strukul, G. Organometallics, 1994, p. 3442.
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7. 6. Martin, V.S., Woodard, S.S., Katsuki, Y., Yamada, Y., Ikeda, M., Sharpless, K.B. J. Am. Chem. Soc., 1981, 103, p. 6237.
8. 7. Bonini, C., Federici, C., Rossi, L., Righi, G. J.Org.Chem., 1995, 60, p. 4803.
9. 2) the mixture was stirred for additional 30 min. Now, t-BuOOH (1.5 mmoles in toluene, ∼ 3.4M solution) was added and the mixture was kept at -20°C for 44 h.The reaction was quenched by stirring with citric acid monohydrate solution (1.5 mmoles in a mixture of 10% acetone in ether) at 20°C for 1 h. The reaction mixture was filtered through a path of celite and purified by column chromatography on silica gel.
10. 9. Cao, Y., Hanson, R.M., Klunder, J.M., Ko, S.Y., Masamune, H., Sharpless, K.B. J. Am. Chem. Soc., 1987, 109, p. 5765.
11. 10. Brunel, J.-M., Diter, P., Duetsch, M., Kagan, H.B. J.Org.Chem., 1995, 60, pp. 8086-8088.
12. 11. Ketone 1 : Amice, P., Conia, J.M., Bull. Soc.Chim France, 1974, pp. 1015-1019. 2: Bindra, J.S., Bindra, R. Prostaglandin synthesis; Academic Press, Inc. New-York, San-Francisco, London 1977, p.269. 3: Newton, F.R., Reynolds, D.P., Grassland, N.M., Kelly, D.R., Roberts, S.M. J.C.S.Chem. Comm., 1979, pp. 683-684. 4: Pigou, P.E., Schiesser, C.H. J.Org.Chem., 1988, 53, pp 3841-3843.
13. Ketone 1 : Amice, P., Conia, J.M., Bull. Soc.Chim France, 1974, pp. 1015-1019. 2: Bindra, J.S., Bindra, R. Prostaglandin synthesis; Academic Press, Inc. New-York, San-Francisco, London 1977, p.269. 3: Newton, F.R., Reynolds, D.P., Grassland, N.M., Kelly, D.R., Roberts, S.M. J.C.S.Chem. Comm., 1979, pp. 683-684. 4: Pigou, P.E., Schiesser, C.H. J.Org.Chem., 1988, 53, pp 3841-3843.
14. Ketone 1 : Amice, P., Conia, J.M., Bull. Soc.Chim France, 1974, pp. 1015-1019. 2: Bindra, J.S., Bindra, R. Prostaglandin synthesis; Academic Press, Inc. New-York, San-Francisco, London 1977, p.269. 3: Newton, F.R., Reynolds, D.P., Grassland, N.M., Kelly, D.R., Roberts, S.M. J.C.S.Chem. Comm., 1979, pp. 683-684. 4: Pigou, P.E., Schiesser, C.H. J.Org.Chem., 1988, 53, pp 3841-3843.
15. Ketone 1 : Amice, P., Conia, J.M., Bull. Soc.Chim France, 1974, pp. 1015-1019. 2: Bindra, J.S., Bindra, R. Prostaglandin synthesis; Academic Press, Inc. New-York, San-Francisco, London 1977, p.269. 3: Newton, F.R., Reynolds, D.P., Grassland, N.M., Kelly, D.R., Roberts, S.M. J.C.S.Chem. Comm., 1979, pp. 683-684. 4: Pigou, P.E., Schiesser, C.H. J.Org.Chem., 1988, 53, pp 3841-3843.
16. 13C NMR δ 30.78 (t, C-2), 36.89 (d, C-3), 62.74 (t, C-5), 70.80 (t, C-4), 177.95 (s. C-I).
17. 13. Conditions: a LKB liquid Chromatograph equipped with a UV spectrometric detector (2158 Uvicord SD; 254 nm. A column Zorbax Sil 4.6x250 mm). Eluent hexane:i-PrOH: water for 5 79.2:20:0.8 and for 7 93.95:5:0.05.
18. 13C NMR δ 30.64 (t, C-2), 34.36 (d, C-3), 64.68 (t, C-4), 69.75 (t, C-5), 175.71 (s, C-1).
19. 20 = -113°. The reference value was taken as a basis for calculating the ee values.
20. 16. Pehk, T., Lippmaa, E., Lopp, M., Paju, A., Borer, B.C., Taylor, R.J.K., Tetrahedron:Asymmetry.1993, 4, 1527.
21. 16.
22. 16.
23. 20 was observed.
24. 19. Haegele, G., Fuhler, R., Lenzen, T. Personal communication.
25. 20. Haigh, C.W., Mallion, R.B. Org.Magn.Res., 1972, 4, p. 203.