Selective oxidation of O-isopropylidene derivatives of diols to 2-hydroxy ketones employing dioxiranes

Tetrahedron Letters

Volumn 37, Issue 1, 1996, Pages 115-118

  Curci, Ruggero ^a   D'Accolti, Lucia ^a   Dinoi, Anna ^a   Fusco, Caterina ^a   Rosa, Angela ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE; KETONE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030059390     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02087-X     Document Type: Article

References (33)

1. For recent reviews, see: (a) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67 , 811.
2. (b) Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. in Organic Peroxides; Ando, W., Ed.; Wiley, New York, 1992 ; Chapter 4, pp 195-219. See references therein.
3. D'Accolti, L.; Detomaso, A.; Fusco, C.; Rosa, A.; Curci, R. J. Org. Chem. 1993, 58, 3600
4. Bovicelli, P.; Lupattelli, P.; Sanetti, A.; Mincione, E. Tetrahedron Lett. 1995, 36, 3031.
5. Kunz, H.; Waldmann, H. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, U.K. (1991); vol. 6, pp 659-662. See references therein.
6. For instance, see: Crispino, G. A.; Ho, P. T.; Sharpless, K. B. Science 1993, 259, 64.
7. (a) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847.
8. (b) Cassidei, L.; Fiorentino, M.; Mello, R.; Sciacovelli, O.; Curci, R. J. Org. Chem. 1987, 52, 699.
9. (c) Adam, W.; Chan, Y.-Y; Cremer, D.; Gauss, J.; Scheutzow, D.; Schindler, M. J. Org. Chem. 1987, 52, 2800.
10. (a) Mello, R.; Fiorentino, M.; Sciacovelli, O.; Curci, R. J. Org. Chem. 1988, 53, 3890.
11. (b) Mello, R.; Fiorentino, M.; Fusco, C.; Curci, R. J. Am. Chem. Soc. 1989, 111, 6749.
12. (a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.; Kwong, H.; Morikawa, K.; Wang, Z. J. Org. Chem. 1992, 57, 2768.
13. (b) Xu, D.; Crispino, G. A.; Sharpless, K. J. Am. Chem Soc. 1992, 114, 7570.
14. (c) Wang, L.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7568.
15. (a) Plattner, J. J.; Rapoport, H. J. Am. Chem Soc. 1971, 93, 1758.
16. (b) Dana, G.; Danechpajouh, H. Bull. Soc. Chim. Fr. 1980, 2, 395.
17. Hanzlick, R. P.; Leinwetter, M. J. Org. Chem. 1978, 43, 438.
18. D +44.9° (c 1.39, MeOH); ee 97%, as determined by GC employing a chiral stationary phase (Beta-DEX™ 120, 0.25 μm film thickness, 30 m × 0.25 mm ID, capillary column).
19. 3); ee 99%, as determined by GC employing a chiral stationary phase (Beta-DEX™ 120, 0.25 μm film thickness, 30 m × 0.25 mm ID, capillary column). For the racemic ketol, see: Pihlaja, K.; Czombos, J. J. Prakt. Chem. 1991, 353, 931.
20. Haiza, M.; Lee, J.; Snyder, J. K. J. Org. Chem. 1990, 55, 5008.
21. D -37.9° (c 1.98, EtOH), ee 92% as determined by HPLC (Hewlett-Packard mod. 1050, UV detector model 35900) employing a chiral stationary phase (DAICEL Chiralcel OD, 25 cm × 0.46 cm ID.; 10% i-PrOH /90% n-hexane, 0.8 mL/min).
22. (a) Ketols (3), (5), (11), (15), (17), see ref. 2, and literature quoted therein
23. -1 (C-OH str.), etc.; MS (70 eV), m/z (r.i.): 144 (1, M+), 101 (3), 111 (1), 59 (100), etc.
24. D -9.5° (c 1.88, MeOH); for the racemic compound, see: Srinivasan, N. S.; Lee, D. G. Synthesis 1979, 520.
25. (d) (13): Tamura, Y.; Annoura, H.; Kondo, H.; Fuji, M.; Yoshida, T.; Fujioka, H. Chem. Pharm. Bull 1987, 35, 2305.
26. Curci, R.; D'Accolti, L.; Fiorentino, M.; Fusco, C.; Adam, W.; González-Nuñez, M. E.; Mello, R., Tetrahedron Lett. 1992, 33 , 4225.
27. (a) Minisci, F.; Zhao, L.; Fontana, F.; Bravo, A. Tetrahedron Lett. 1995, 36, 1697.
28. (b) Bravo, A.; Fontana, F.; Fronza, G.; Mele, A.; Minisci, F. J. Chem. Soc., Chem. Comm. 1995, 1573.
29. -1 etc.; MS (70 eV), m/z (r.i.): 339 (4), 177 (17), 176 (60), 119 (64), 91 (100), 77 (24), 43 (39), etc.
30. -1, etc.
31. For instance, see : (a) Hannessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon : New York, 1983; Chapter 2.
32. (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876.
33. (c) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.