Direct asymmetric α-hydroxylation of β-hydroxyketones

Tetrahedron Letters

Volumn 38, Issue 28, 1997, Pages 5051-5054

  Lopp, Margus ^a   Paju, Anne ^a   Kanger, Tõnis ^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

KETOL;

ARTICLE; ENANTIOMER; HYDROXYLATION; KETOGENESIS; STEREOCHEMISTRY;

EID: 0030813317     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01102-7     Document Type: Article

References (13)

1. Lopp M., Paju A., Kanger T., Pehk, T. Tetrahedron Lett., 1996, 37, 7583-7486.
2. Compounds 1a and 1b were prepared according to Taylor R.J.K., Wiggins, K., Robinson, D.H. Synthesis., 1990, 589-590; 1c was purchased from Aldrich.
3. Davis, F.A., Chen, B.-C. Chem.Rev., 1992, 92, 919-934.
4. Cao, Y., Hanson, R.M., Klunder, J.M., Ko, S.Y., Masamune ,H., Sharpless, K.B. J.Am.Chem.Soc., 1987, 109, 5765.
5. 2 (2 ml) the mixture was stirred for 30 min. Now t-BuOOH (1.2 mmoles in toluene,∼3.4 M solution) was added and the mixture was kept at -20°C for 46 h. The reaction was quenched by stirring with citric acid monohydrate solution (3 mmoles in a mixture of 10% acetone in ether) at room temperature for 1 h. The reaction mixture was filtered through a path of celite, the celite layer was washed with acetone and methanol. The solutes were concentrated and the residue was purified on silica gel.
6. Shultz, M. Kluge, R., Scüβler, M., Hoffmann, G., Tetrahedron, 1995, 51, 3175-3180.
7. Hashiyama, T, Morikawa, K., Sharpless, K.B. J.Org.Chem., 1992, 57, 5067-5068.
8. Fukuda T., Katsuki T. Tetrahedron Lett., 1996, 25, 4389-4392; Adam, W., Frell, R.T., Mock-Knoblauch C., Saha-Möller, C.H. Tetrahedron Lett., 1996, 36, 6531-6534.
9. Fukuda T., Katsuki T. Tetrahedron Lett., 1996, 25, 4389-4392; Adam, W., Frell, R.T., Mock-Knoblauch C., Saha-Möller, C.H. Tetrahedron Lett., 1996, 36, 6531-6534.
10. For example a recent work by Gala D., DiBenedetto D.J., Mergelsberg I., Kugelman, M. Tetrahedron Lett., 1996, 45, 8117-8120.
11. 3).
12. 3), 82.33 (CHO), 135.87 (s-Ph), 127.09 (o-Ph), 128.69 (m-Ph), 128.92 (p-Ph), 170.31 (COO).
13. Finn, M.G., Sharpless, K.B. On the Mechanism of Asymmetric Epoxidation with Titanium-Tartrate Catalysts. In: Asymmetric Synthesis; Morrisson ,J.D., Ed.; Academic Press, New York, 1985; p. 247.