One-pot synthesis and resolution of chiral allylic alcohols

Tetrahedron Asymmetry

Volumn 14, Issue 18, 2003, Pages 2839-2844

  Kamal, Ahmed ^a   Sandbhor, Mahendra ^a   Shaik, Ahmad Ali ^a   Sravanthi, V ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 (1 PHENYLMETHYLIDENE) 1 CYCLOHEXANOL; 2 (1 PHENYLMETHYLIDENE) 1 CYCLOHEXYL ACETATE; 2 ACETOXY 4 (1 NAPHTHYL) 3 BUTENE; 2 ACETOXY 4 (3 PHENOXYPHENYL) 3 BUTENE; 2 ACETOXY 4 CHLOROPHENYL 3 BUTENE; 2 ACETOXY 4 PHENYL 3 BUTENE; 4 (1 NAPHTHYL) 3 BUTEN 2 OL; 4 (3 PHENOXYPHENYL) 3 BUTEN 2 OL; 4 CHLOROPHENYL 3 BUTEN 2 OL; 4 PHENYL 3 BUTEN 2 OL; ALLYL ALCOHOL; DIISOPROPYL ETHER; INFUSORIAL EARTH; KETONE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; BURKHOLDERIA CEPACIA; CATALYSIS; CHEMICAL REACTION KINETICS; ENANTIOSELECTIVITY; NONHUMAN; PRECURSOR; PRIORITY JOURNAL; SCREENING; SUBSTITUTION REACTION; TRANSESTERIFICATION;

EID: 1542603947     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00598-6     Document Type: Article

References (25)

1. Hoveyda A.H., Evans D.A., Fu G.C. Chem Rev. 93:1993;1307.
2. Fehr C., Galindo J. Angew. Chem., Int. Ed. 39:2000;569.
3. Bach J., Berenguer R., Garcia J., Vilarrasa J. Tetrahedron Lett. 36:1995;3425.
4. Aleu J., Bergamo B., Brenna E., Fuganti C., Serra S. Eur. J. Org. Chem. 2000;3031.
5. Brenna E., Fuganti C., Grasselli P., Serra S. Eur. J. Chem. 2001;1349.
6. Hage A., Petra D.G.I., Field J.A., Schipper D., Wijnberg J.B.P.A., Kamer P.C.J., Reek J.N.H., Leeuwen P.W.N.M., Wever R., Schoemaker H.E. Tetrahedron: Asymmetry. 12:2001;1025.
7. Noyori R., Ohkuma T. Angew. Chem., Int. Ed. 40:2001;40.
8. Lee D., Huh E.A., Kim M., Jung H.M., Koh J.H., Park J. Org. Lett. 2:2000;2377.
9. Gao Y., Hanson R.M., Klunder J.M., Ko S.Y., Masamune H., Sharpless K.B. J. Am. Chem. Soc. 109:1987;5765.
10. Ghanem A., Schurig V. Tetrahedron: Asymmetry. 14:2003;57.
11. Lindner E., Ghanem A., Warad I., Eichele K., Mayer H.A., Schurig V. Tetrahedron: Asymmetry. 14:2003;1045.
12. Burgess K., Jennings L.D. J. Am. Chem. Soc. 113:1991;6129.
13. Itoh T., Akasaki E., Nishimura Y. Chem. Lett. 2002;154.
14. Kamal A., Sandbhor M., Ramana K.V. Tetrahedron: Asymmetry. 13:2002;815.
15. Kamal A., Sandbhor M. Bioorg. Med. Chem. Lett. 12:2002;1735.
16. Kamal A., Sandbhor M., Shaik A.A. Tetrahedron: Asymmetry. 14:2003;1575.
17. Aramini A., Brinchi L., Germani R., Savelli G. Eur. J. Org. Chem. 2000;1793.
18. Activated alumina was prepared according to Ref. 7a.
19. Faber K. Biotransformations in Organic Media. 3rd ed. 1996;Springer, Graz, Austria.
20. Kvittingen L. Tetrahedron. 50:1994;8253.
21. Rubio E., Alfonso F.M., Klibanov A.M. J. Am. Chem. Soc. 113:1991;695.
22. Determined by chiral HPLC (Chiracel OD column, Daicel) at 254 nm wavelength employing hexane-isopropanol (80:20) as mobile phase (a) At 0.5 mL/min flow and 13 kgf pressure. (b) At 0.7 mL/min flow and 18 kgf pressure.
23. Chen C.-S., Funjimoto Y., Girdaunkar G., Sih C.J. J. Am. Chem. Soc. 104:1982;7294.
24. Determined by chiral HPLC (Chiracel OB-H column, Daicel) at 254 nm wavelength employing hexane-isopropanol (80:20) as mobile phase, 0.5 mL/min flow and 23 kgf pressure.
25. Determined by chiral HPLC (Chiracel, OJ-H column, Daicel) at 254 nm wavelength employing hexane-isopropanol (90:10) as mobile phase, 0.5 mL/min and 18 kgf pressure.