Regioselective oxidation of azidodiols, bromodiols and triol derivatives by dimethyldioxirane

Tetrahedron

Volumn 54, Issue 47, 1998, Pages 14301-14314

  Bovicelli, Paolo ^a   Truppa, Danilo ^a   Sanetti, Anna ^b   Bernini, Roberta ^b   Lupattelli, Paolo ^c  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF TUSCIA   (Italy)

^c UNIVERSITY OF BASILICATA   (Italy)

Author keywords

Diols; Dioxiranes; Triols

Indexed keywords

AZIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; OXIDATION; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032211302     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00885-0     Document Type: Article

References (16)

1. [1] Bovicelli P, Sanetti A, Lupattelli P. Tetrahedron 1996; 52, 10969-10978.
2. [2] Bovicelli P, Lupattelli P, Sanetti A, Mincione E. Tetrahedron Lett. 1995; 36: 3031-3034.
3. [3] Bovicelli P, Ballini R, Papa F. Tetrahedron Lett. 1996; 37: 3507-3510.
4. [4] Bach RD, Andres JL, Su MD, McDouall JW. J. Am. Chem. Soc. 1993; 115: 5768.
5. [5] Curci R, D'Accolti L, Dinoi A, Fusco C, Rosa A. Tetrahedron Lett. 1996; 37: 115-118.
6. [6] Sharpless K.B, Amberg W, Bennani YL, Crispino GA, Hartung J, Jeong KS, Kwong HL, Morikawa K, Wang ZM, Xu D, Zhang XL. J. Org. Chem. 1992; 57: 2768-2771.
7. th ed., John Wiley and Sons, New York, 1992, p. 393.
8. [8] March J. ibid. , p. 386.
9. [9] March J. ibid. , p. 822.
10. [10] Brown HC, Bhat KS. J. Org. Chem. 1986; 51: 445-449.
11. th ed.,John Wiley and Sons, New York, 1992, p. 826.
12. [12] Bahrens CH, Sharpless KB. J. Org. Chem. 1985; 50 (26): 5697-5704.
13. [13] This compound was prepared according to the procedure described in Payne GB. J. Am. Chem. Soc. 1959: 4901.
14. [14] Bonini, C.; Righi, G.; Chionne, A. private communication.
15. [15] Curci R, Dinoi A, Rubino MF. Pure Appl. Chem. 1995; 67: 811-821.
16. [16] Dimethyldioxirane solution was prepared as reported in Adam W, Bialas J, Hadijarapoglou LP. Chem. Ber. 1991; 124: 2377.