Stereoselective sulfoxide directed reduction of 1,2-diketo-derivatives to enantiomerically pure syn and anti 1,2-diols. Correction of the relative configuration by X-ray and chemical correlation to goniobutenolides A and B

Tetrahedron Letters

Volumn 40, Issue 1, 1999, Pages 177-180

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

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BUTENOLIDE; DIKETONE; GLYCOL; METHOXYAMINE; NATURAL PRODUCT; OXALIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; ENANTIOMER; REACTION ANALYSIS; REACTION TIME; REDUCTION; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0032890484     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)80052-X     Document Type: Article

References (11)

1. Solladié, G., Hanquet, G., Rolland, C. Tetrahedron Lett. 1997, 38, 5847-5850.
2. Solladié, G., Demailly, G., Greck, C., J.Org.Chem. 1985, 50, 1552-1554; Solladié, G., Almario, A., Tetrahedron Lett. 1994, 35, 1937-1940. Solladié, G., Huser, N., Fischer, J. Decian, A., J. Org. Chem. 1995, 60, 4988-4990.
3. Solladié, G., Demailly, G., Greck, C., J.Org.Chem. 1985, 50, 1552-1554; Solladié, G., Almario, A., Tetrahedron Lett. 1994, 35, 1937-1940. Solladié, G., Huser, N., Fischer, J. Decian, A., J. Org. Chem. 1995, 60, 4988-4990.
4. Solladié, G., Demailly, G., Greck, C., J.Org.Chem. 1985, 50, 1552-1554; Solladié, G., Almario, A., Tetrahedron Lett. 1994, 35, 1937-1940. Solladié, G., Huser, N., Fischer, J. Decian, A., J. Org. Chem. 1995, 60, 4988-4990.
5. Dana, G., Danechpajouh, H., Bull.Soc.Chim. Fr. 1980, 395-399.
6. 2), 123.95 to 141.82 (arom. CH and C).
7. Fang, X.P., Anderson, J.E., Chang, C.J., McLaugnlin, J.L. Tetrahedron 1991, 47,; 9751-9758; Xu, D., Sharpless, B. Tetrahedron Lett. 1994, 35, 4685-4688; Shing, T.K.M., Tai, W.W.-F., Tsui, H.-C. J. Chem. Soc., Chem. Commun. 1994, 1293-1294; Ko, S.Y., Lerpinière, J. Tetrahedron Lett. 1995, 36, 2101-2104.
8. Fang, X.P., Anderson, J.E., Chang, C.J., McLaugnlin, J.L. Tetrahedron 1991, 47,; 9751-9758; Xu, D., Sharpless, B. Tetrahedron Lett. 1994, 35, 4685-4688; Shing, T.K.M., Tai, W.W.-F., Tsui, H.-C. J. Chem. Soc., Chem. Commun. 1994, 1293-1294; Ko, S.Y., Lerpinière, J. Tetrahedron Lett. 1995, 36, 2101-2104.
9. Fang, X.P., Anderson, J.E., Chang, C.J., McLaugnlin, J.L. Tetrahedron 1991, 47,; 9751-9758; Xu, D., Sharpless, B. Tetrahedron Lett. 1994, 35, 4685-4688; Shing, T.K.M., Tai, W.W.-F., Tsui, H.-C. J. Chem. Soc., Chem. Commun. 1994, 1293-1294; Ko, S.Y., Lerpinière, J. Tetrahedron Lett. 1995, 36, 2101-2104.
10. Fang, X.P., Anderson, J.E., Chang, C.J., McLaugnlin, J.L. Tetrahedron 1991, 47,; 9751-9758; Xu, D., Sharpless, B. Tetrahedron Lett. 1994, 35, 4685-4688; Shing, T.K.M., Tai, W.W.-F., Tsui, H.-C. J. Chem. Soc., Chem. Commun. 1994, 1293-1294; Ko, S.Y., Lerpinière, J. Tetrahedron Lett. 1995, 36, 2101-2104.
11. 2), 71.44 (CHOSi), 77.74 ( CHOH), 123.88 to 142.23 (arom. C and CH).