Homobenzotetramisole: An effective catalyst for kinetic resolution of aryl-cycloalkanols

Organic Letters

Volumn 10, Issue 6, 2008, Pages 1115-1118

  Birman, Vladimir B ^a   Li, Ximin ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; BENZOTETRAMISOLE; DRUG DERIVATIVE; TETRAMISOLE;

ARTICLE; CATALYSIS; CHEMISTRY; KINETICS; STRUCTURE ACTIVITY RELATION; TEMPERATURE;

ALKANES; CATALYSIS; KINETICS; STRUCTURE-ACTIVITY RELATIONSHIP; TEMPERATURE; TETRAMISOLE;

EID: 45549099652     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol703119n     Document Type: Article

References (18)

1. (a) Birman, V. B.; Uffman, E. W.; Jiang, H.; Li, X.; Kilbane, C. J. J. Am. Chem. Soc. 2004, 126, 12226.
2. (b) Birman, V. B.; Jiang, H. Org. Lett. 2005, 7, 3445.
3. (c) Birman, V. B.; Li, X. Org. Lett. 2006, 8, 1351.
4. (d) Birman, V. B.; Jiang, H.; Li, X.; Guo, L.; Uffman, E. W. J. Am. Chem. Soc. 2006, 128, 6536.
5. (e) Birman, V. B.; Guo, L. Org. Lett. 2006, 8, 4859.
6. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249.
7. For review of nonenzymatic kinetic resolution of alcohols and alternative catalyst designs, see: Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974.
8. Birman, V. B.; Li, X.; Han, Z. Org. Lett. 2007, 9, 37.
9. Kobayashi, M.; Okamoto, S. Tetrahedron Lett. 2006, 47, 4347.
10. Liu, S.; Müller, J. F. K.; Neuburger, M.; Schaffner, S.; Zehnder, M. Helv. Chim. Acta. 2000, 83, 1256.
11. McKay, A. F.; Whittingham, D. J.; Kreling, M. -E. J. Am. Chem. Soc. 1958, 80, 3339.
12. For enzymatic kinetic resolution of 24 and its utility as a chiral auxiliary, see: Whitesell, J. K.; Chen, H. -H.; Lawrence, R. M. J. Org. Chem. 1985, 50, 4663.
13. Efficient nonenzymatic kinetic resolution of 24 has been previously reported by: (a) Oriyama, T.; Hori, Y.; Imai, K.; Sasaki, R. Tetrahedron Lett. 1996, 37, 8543 (s =200).
14. (b) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496 (s > 50).
15. (c) Jeong, K. -S.; Kim, S. -H.; Park, H. -J.; Chang, K. -J.; Kim, K. S. Chem. Lett. 2002, 1114 (s = 21).
16. Vedejs, E.; and Daugulis, O. J. Am. Chem. Soc. 2003, 125, 4166.
17. For use of tert-amyl alcohol as a solvent for KR, see, e.g.: Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794.
18. Interestingly, BTM produced higher enantioselectivity in this case, although the reaction was quite slow (s = 9.9 at 15% conversion after 8 h at rt; 8 mol % catalyst loading).