Tishchenko reactions and Oppenauer oxidation reactions of aldehydes promoted by diisobutylaluminum hydride

Tetrahedron Letters

Volumn 45, Issue 16, 2004, Pages 3313-3315

  Hon, Yung Son ^a,b   Chang, Chun Ping ^a   Wong, Ying Chieh ^a  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

^b INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

silyloxyaldehyde; silyloxyketone; Oppenauer oxidation; Tishchenko reaction

Indexed keywords

ALDEHYDE; ALUMINUM; KETONE; PENTANE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; ENVIRONMENTAL TEMPERATURE; MOLECULAR MECHANICS; OPPENAUER OXIDATION; SOLVATION;

EID: 1642619502     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.145     Document Type: Article

References (44)

1. Villani F.J., Nord F.F. J. Am. Chem. Soc. 69:1947;2605-2607. and references cited therein.
2. Ogata Y., Kawasaki A., Kishi I. Tetrahedron. 23:1967;825-830.
3. Lin I., Day A.R. J. Am. Chem. Soc. 74:1952;5133-5135.
4. Saegusa T., Ueshima T. J. Org. Chem. 33:1968;3310-3311.
5. Baidossi W., Rosenfeld A., Wassermann B.C., Schutte S., Schumann H., Blum J. Synthesis. 1996;1127-1130.
6. Ooi T., Miura T., Takaya K., Marouka K. Tetrahedron Lett. 40:1999;7695-7698.
7. Ooi T., Ohmatsu K., Sasaki K., Miura T., Marouka K. Tetrahedron Lett. 44:2003;3191-3193.
8. Shirakawa S., Takai J., Sasaki K., Miura T., Maruoka K. Hetreocycles. 59:2003;57-61.
9. For a review, see: Chang C.P., Hon Y.S. Chemistry (The Chinese Chem. Soc., Taipei). 60:2002;561-572.
10. Bunce R.A., Shellhammer A. Jr. J. Org. Prep. Proc. Int. 19:1987;161-166.
11. Törmäkangas O.P., Koskinen A.M.P. Tetrahedron Lett. 42:2001;2743-2746.
12. Tanabe K., Saito K. J. Catal. 35:1974;247-253.
13. Tsuji H., Yagi F., Hattori H., Kita H. J. Catal. 148:1994;759-770.
14. Seki T., Akutu K., Hattori H. Chem. Commun. 2001;1000-1001.
15. Törmäkangas O.P., Saarenketo P., Koskinen A.M.P. Org. Process Res. Dev. 6:2002;125-131.
16. Stapp P.R. J. Org. Chem. 38:1973;1433-1434.
17. Jedlinski Z., Kowalczuk M. J. Org. Chem. 44:1979;222-224.
18. Kabashima H., Tsuji H., Nakata S., Tanaka Y., Hattori H. Appl. Catal. A: Gen. 194/195:2000;227-240.
19. Morita K.I., Nishiyama Y., Ishii Y. Organometallics. 12:1993;3748-3752.
20. Umekawa Y., Sakaguchi S., Nishiyama Y., Ishii Y. J. Org. Chem. 62:1997;3409-3412.
21. Yokoo K., Mine N., Taniguchi H., Fujiwara Y. J. Organomet. Chem. 279:1985;C19-C21.
22. Onozawa S.Y., Sakakura T., Tanaka M., Shiro M. Tetrahedron. 52:1996;4291-4302.
23. Berberich H., Roesky P.W. Angew. Chem., Int. Ed. 37:1998;1569-1571.
24. Gillespie K.M., Munslow I.J., Scott P. Tetrahedron Lett. 40:1999;9371-9374.
25. Evans D.A., Hoveyda A.H. J. Am. Chem. Soc. 112:1990;6447-6449.
26. Curran D.P., Wolin R.L. Synlett. 1991;317-318.
27. Takeno M., Kikuchi S., Morita K., Nishiyama Y., Ishii Y. J. Org. Chem. 60:1995;4974-4975.
28. Uenishi J.-I., Masuda S., Wakabayashi S. Tetrahedron Lett. 32:1991;5097-5100.
29. Hsu J.-L., Fang J.-M. J. Org. Chem. 66:2001;8573-8584.
30. Smith A.B. III, Lee D., Adams C.M., Kozlowski M.C. Org. Lett. 4:2002;4539-4541.
31. Villacorta G.M., Filippo J.S. Jr. J. Org. Chem. 48:1983;1151-1154.
32. Yamashita M., Watanabe Y., Mitsudo T.A., Takegami Y. Bull. Chem. Soc. Jpn. 49:1976;3597-3600.
33. Bankston D. J. Org. Chem. 54:1989;2003-2005.
34. Morino H., Ito T., Yamamoto A. Chem. Lett. 1978;17-20.
35. Ito T., Horino H., Koshino Y., Yamamoto A. Bull. Chem. Soc. Jpn. 55:1982;504-512.
36. Grushin V.V., Alper H. J. Org. Chem. 56:1991;5159-5161.
37. Grigg R., Mitchell T.R.B., Suthivaiyakit S. Tetrahedron. 37:1981;4313-4319.
38. Maussoui M., Beaupere D., Nadjo L., Uzan R. J. Organomet. Chem. 259:1983;345-353.
39. Bergens S.H., Fairlie D.P., Bosnich B. Organometallics. 9:1990;566-571.
40. Bernard K.A., Atwood J.D. Organometallics. 7:1988;235-236.
41. Burkhardt E.R., Bergman R.G., Heathcock C.H. Organometallics. 9:1990;30-44.
42. Tsuda T., Habu H., Saegusa T. Chem. Commun. 1974;620-620.
43. Ermolenko L., Sasaki N.A., Potier P. Synlett. 2001;1565-1566.
44. Djerrassi C. Org. React. 6:1951;207-272.