Stereoselective sulfoxide directed reduction of 1,2-diketo-derivatives to enantiomerically pure syn and anti 1,2-diols

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5847-5850

  Solladié, Guy ^a   Hanquet, Gilles ^a   Rolland, Catherine ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE; SULFOXIDE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030757286     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01300-2     Document Type: Article

References (13)

1. Solladié, G., Almario, A., Tetrahedron Lett. 1994, 35, 1937-1940.
2. Sibi, M.P., Marwin, M., Sharma, R., J. Org. Chem. 1995, 60, 5016-5023.
3. Solladié, G., Hutt, J., Giraidin, A., Synthesis 1987, 173.
4. 1H NMR of the crude product.
5. 2); 64,09 (CH); 124,05 (CH arom); 130,13 (CH arom) 140,92 and 141,71 (C arom); 174,03 (C = O).
6. 8 the reverse stereoselectivity for the carbonyl reduction : by reduction with DIBAL in presence of zinc bromide, chloride or iodide the diastereomer (R,S)-3 was still obtained as the main product but with a lower diastereoselectivity, probably due to the Zn chelation on the vicinal amide and not on the sulfoxide.
7. Nahm, S., Weinreb, S.B., Tetrahedron Lett. 1981, 22, 3815-3818.
8. Solladié, G., Demailly, G., Greck, C., J.Org.Chem. 1985, 50, 1552-1554; Solladié, G., Huser, N., Fischer, J. Decian, A., J. Org. Chem. 1995, 60, 4988-4990.
9. Solladié, G., Demailly, G., Greck, C., J.Org.Chem. 1985, 50, 1552-1554; Solladié, G., Huser, N., Fischer, J. Decian, A., J. Org. Chem. 1995, 60, 4988-4990.
10. Davies, F. A., Sheppard, A.C., J.Org.Chem. 1987, 52, 954-955.
11. 2); 70,21 and 70,64 (CH); 123,90 and 130,14 ((CH arom); 141,22 and 141,62 (C arom).
12. 2-SO), 75.36 (CH-O), 75.86. (CH-O), 108.60 (C-0), 123.14 (arom.CH), 129.29 (arom. CH), 140.50 (arom.C), 141.07 (arom.C).
13. Dana, G., Danechpajouh, H., Bull.Soc.Chim. Fr. 1980, 395-399.