Asymmetric synthesis of syn and anti 1,2-diols from diethyl oxalate using the stereoselective sulfoxide directed reduction of 1,2-diketone derivatives

Tetrahedron Letters

Volumn 40, Issue 15, 1999, Pages 3071-3074

  Solladié, Guy ^a   Hanquet, Gilles ^a   Izzo, Irene ^a,b   Crumbie, Robyn ^a,c  

^a CNRS   (France)

^b UNIVERSITY OF SALERNO   (Italy)

^c UNIVERSITY OF WESTERN SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; DIKETONE; GLYCOL; MURICATACIN; NATURAL PRODUCT; OXALIC ACID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; SULFINIC ACID DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG ISOLATION; DRUG SYNTHESIS; ENANTIOMER; NONHUMAN; PLANT SEED; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0033537817     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00368-8     Document Type: Article

References (20)

1. a) Solladié G, Hanquet, G.; Rolland, C. Tetrahedron Lett. 1997, 38, 5847-5850;
2. b) Solladié G.; Hanquet, G.; Rolland, C. Tetrahedron Lett. 1999, 40, 177-180.
3. For reaction of long chain Grignard reagents on Weinreb amids see Sharma, R.; Marquez, V.E.; Org. Prep. Proc., Int., 1994, 26, 611-615.
4. Solladié. G.; Hutt, J.; Girardin, A. Synthesis, 1987, 173.
5. Solladié. G.; Almario, A. Tetrahedron Lett. 1994, 35, 1937-1940.
6. Yamanoi, T.; Akiyama, T.; Ishida, E.; Abe, H.; Amemiya, M.; Inazu, T. Chem. Lett., 1989, 335-336.
7. 2-SO), 74.83 (CH-O), 82.38 (CH-O), 108.74 (i-Pr C), 123.93 (arom. CH), 125.12 (vinylic CH), 130.16 (arom. CH), 138.53 (vinylic CH), 141.36 (arom. C), 141.80 (arom. C).
8. Rieser, M.J.; Kozlowski, J.F.; Wood K.V.; Mc Laughlin, J.L. Tetrahedron Lett. 1991, 32, 1137-1140.
9. Previous syntheses : a) Rassu, G. ; Pinna, L. Spanu. P. ; Zanardi, F. ; Battistini, L. ; Casiraghi, G. J. Org. Chem. 1997, 62, 4513-4517;
10. b) Somfai, P. J. Chem. Soc., Perkin Trans. 1 1995, 817-819;
11. c) Bonini, C.; Federici, C.; Rossi, L.; Righi, G. J. Org. Chem. 1995, 60, 4803-4812;
12. c) Quayle, P.; Rahman, S.; Herbert, J. Tetrahedron Lett. 1995, 36, 8087-8088;
13. d) Marshall, J.A. ; Welmaker. G.S. J. Org. Chem. 1994, 59, 4122-4125;
14. e) Marshall, J.A. ; Welmaker, G.S. Synlett 1992, 537-538;.
15. f) Wang, Z.-M.; Zhang, X.-L.; Sharpless, K.B.; Sinha, S.C.; Sinha-Bagchi, A.; Keinan, E. Tetrahedron Lett. 1992, 33, 6407-6410;
16. g) Scholz, G.; Tochtermann, W. Tetrahedron Lett. 1991, 32, 5535-5538;
17. h) Szlosek, M.S.; Franck, X.; Figadère. B.; Cavé, A. J. Org. Chem. 1998, 63, 5169-5172;
18. i) Saniere. M.; Charvet, I.; Le Merrer, Y.; Depezay, J.C. Tetrahedron 1995, 51, 1653-1662.
19. a) Saïah, M.; Bessades, M. :Antonakis, K. Tetrahedron Lett. 1993, 34, 1597-1598;
20. b) Figadère, B.; Harmange, J.-C; Laurens, A.; Cavé, A. Tetrahedron Lett. 1991, 32, 7539-7542,