An efficient and convenient protocol for highly regioselective cleavage of terminal epoxides to β-Halohydrins

Synlett

Volumn , Issue 9, 2009, Pages 1511-1513

  Wang, Tao ^a   Ji, Wen Hao ^a   Xu, Zhong Yu ^a   Zeng, Bu Bing ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

halohydrin; Chemoselectivity; Cleavage; Epoxide; Regioselectivity

Indexed keywords

BETA HALOHYDRIN; EPOXIDE; FUNCTIONAL GROUP; HALIDE; MAGNESIUM SALT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; REGIOSELECTIVITY; RING OPENING; ROOM TEMPERATURE; SYNTHESIS;

EID: 67649321668     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217182     Document Type: Article

References (24)

1. (a) Piva, O. Tetrahedron Lett. 1992, 33, 2459.
2. (b) Berkessel, A.; Rollmann, C.; Chamouleau, F.; Labs, S.; May, O.; Gröger, H. Adv. Synth. Catal. 2007, 349, 2697.
3. (c) de Jong, R. M.; Tiesinga, J. J. W.; Villa, A.; Tang, L.; Janssen, D. B.; Dijkstra, B. W. J. Am.Chem. Soc. 2005, 127, 13338.
4. For reviews, see: (a) Moore, R. E. In Marine Natural Products, Vol.1; Scheuer, P. J., Ed.; Academic: New York, 1978, Chap. 2.
5. (b) Fenical, W. In Marine Natural Products, Vol.2; Scheuer, P. J., Ed.; Academic: New York, 1980, 174.
6. (c) Barrow, K. D. In Marine Natural Products, Vol.5; Scheuer, P. J., Ed.; Academic: New York, 1983, 51.
7. (a) Righi, G.; Franchini, T.; Bonini, C. Tetrahedron Lett. 1998, 39, 2385.
8. (b) Babudri, F.; Fiandanese, V.; Marchese, G.; Punzi, A. Tetrahedron 2001, 57, 549.
9. (c) Boukhris, S.; Souizi, A. Tetrahedron Lett. 2003, 44, 3259.
10. (a) Sharghi, H.; Eskandari, M. M. Tetrahedron 2003, 59, 8509.
11. (b) Konnaklieva, M. L.; Dahi, M. L.; Turos, E. Tetrahedron Lett. 1992, 33, 7093.
12. (c) Stewart, C. A.; Vander Werf, C. A. J. Am. Chem. Soc. 1954, 76, 1259.
13. (d) Kotsuki, H.; Shimanouchi, T. Tetrahedron Lett. 1996, 37, 1845.
14. (e) Sabitha, G.; Babu, R. S.; Rajkumar, M.; Reddy, C. S.; Yadav, J. S. Tetrahedron Lett. 2001, 42, 3955.
15. (f) Pinto, R. M. A.; Salvador, J. A. R.; Roux, C. L. Tetrahedron 2007, 63, 9221.
16. (g) Das, B.; Krishnaiah, M.; Venkateswarlu, K. Tetrahedron Lett. 2006, 47, 4457.
17. (a) Wu, J.; Sun, X.; Sun, W.; Ye, S. Synlett 2006, 2489.
18. (b) Niknam, K.; Nasehi, T. Tetrahedron 2002, 58, 10259.
19. Bajwa, J. S.; Anderson, R. C. Tetrahedron Lett. 1991, 32, 3021.
20. (a) Ranu, B. C.; Banerjee, S. J. Org. Chem. 2005, 70, 4517.
21. (b) Ranu, B. C.; Adak, L.; Banerjee, S. Can. J. Chem. 2007, 85, 366.
22. 2 to give the product.
23. 3): δ = 72.4, 70.9, 48.5, 36.5, 34.8, 29.5, 25.8, 25.6, 24.7, 18.1, 16.6, -4.4, -4.6.
24. Eisch, J. J.; Liu, Z. R.; Zheng, G. X. J. Org. Chem. 1992, 57, 5140.