Regioselective ring-opening of 2,3-epoxy alcohols with tetramethylammonium triacetoxyborohydride

Heterocycles

Volumn 48, Issue 9, 1998, Pages 1753-1757

  Honda, Toshio ^a   Mizutani, Hirotake ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005226390     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-98-8263     Document Type: Article

References (17)

1. C. H. Behrens, S. Y. Ko, K. B. Sharpless, and F. J. Walker, J. Org. Chem., 1985, 50, 5687;
2. C. H. Behrens and K. B. Sharpless, Pure & Appl. Chem., 1983, 55, 589.
3. M. Caron and K. B. Sharpless, J. Org. Chem., 1985, 50, 1557.
4. Introduction of an oxygen function: (a) E. Alvarez, M. T. Nuñez, and V. S. Martín, J. Org. Chem., 1990, 55, 3429.
5. (b) Y. E. Raifeld, A. Nikitenko, and B. M. Arshava, Tetrahedron:Asymmetry, 1991, 2, 1083.
6. (c) Y. E. Raifeld, A. Nikitenko, and B. M. Arshava, Tetrahedron, 1990, 49, 2509.
7. (d) J. M. Palazon, B. Añnorbe, and V. S. Martín, Tetrahedron Lett., 1986, 27, 4987.
8. (e) S. Y. Ko and K. B. Sharpless, J. Org. Chem., 1986, 51, 5413;
9. Introduction of a halogen atom: see (3a) and (f) K. S. Kirshenbaum and K. B. Sharpless, Chemistry Lett., 1987, 11;
10. Introduction of a nitrogen function: see (3e) and (g) M. Canas, M. Poch, X. Verdaguer, A. Moyano, M. A. Paricás, and A. Riera, Tetrahedron Lett., 1991, 32, 6931.
11. (h) M. Caron, P. R. Carlier, and K. B. Sharpless, J. Org. Chem., 1988, 53, 5185.
12. T. K. Chakraborty and G. V. Reddy, Tetrahedron Lett., 1990, 31, 1335;
13. Introduction of s sulfide group: see (3e) and (3g); Introduction of hydride: (j) L. -x. Dai, B. -L. Lou, Y. -z. Zhang, and G. -z. Guo, Tetrahedron Lett., 1986, 27, 4343.
14. Introduction of a halogen atom was reported using monochloroborane-dimethyl sulfide: P. Bovicelli, P. Lupattelli, M. T. Bersani, and E. Mincione, Tetrahedron Lett., 1992, 33, 6181.
15. T. Honda, M. Ohta, and H. Mizutani, Heterocycles, 1997, 46, 137.
16. D. A. Evans, K. T. Chapman, and E. M. Carreira, J. Am. Chem. Soc., 1988, 110, 3560.
17. 1H NMR spectrum.