Resolution of β-aminoalcohols and 1,2-diamines using fractional crystallization of diastereomeric salts of dehydroabietic acid

Tetrahedron Asymmetry

Volumn 14, Issue 21, 2003, Pages 3297-3300

  Guangyou, Zhang ^a,b   Yuquing, Liao ^a   Zhaohui, Wang ^a   Nohira, Hiroyuki ^a   Hirose, Takuji ^a  

^a SAITAMA UNIVERSITY   (Japan)

^b UNIVERSITY OF JINAN   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINO 3 PHENYLOXY 2 PROPANOL; 1,2 DIAMINOCYCLOHEXANE; 2 AMINOCYCLOHEXANOL; AMINOALCOHOL; AMINOPROPANOL; DEHYDROABIETIC ACID; DIAMINE; PHENYLETHANOLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CRYSTALLIZATION; DIASTEREOISOMER; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH TEMPERATURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0142227158     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.08.033     Document Type: Article

References (24)

1. Sheldon R.A. Chirotechnology - Industrial Synthesis of Enantiomerically Active Compounds. 1993;Marcel Dekker, New York.
2. Saigo K., Okuda Y., Wakabayashi S., Hoshiko T., Nohira H. Chem. Lett. 1981;857.
3. Saigo K., Miura H., Ishizaki K., Nohira H. Bull. Chem. Soc. Jpn. 55:1982;1188.
4. Saigo K., Ogawa S., Kikuchi S., Kasahara A., Nohira H. Bull. Chem. Soc. Jpn. 55:1982;1568.
5. Konno Y., Tominaga T., Murata T., Aoki Y., Hirose T., Nohira H. Enantiomer. 3:1998;181.
6. Shitara H., Aoki Y., Hirose T., Nohira H. Bull. Chem. Soc. Jpn. 73:2000;259.
7. Aoki Y., Nomoto S., Hirose T., Nohira H. Mol. Cryst. Liq. Cryst. 346:2000;35.
8. Asep R., Aoki Y., Hirose T., Nohira H. Mol. Cryst. Liq. Cryst. 346:2000;51.
9. Condra J.H., Shleif W.A., Blahy O.M., Gabryelski L.J., Graham D.J., Quitero J.C., Rhodes A., Robbins H.L., Roth E., Shivaprakash M., Titus D., Yang T., Tepper H., Squires K.E., Deutsh P.J., Emili E.A. Nature. 374:1995;569.
10. Ghosh A.K., Liu W. J. Org. Chem. 61:1996;6175.
11. Vineyard B.D., Knowles W.S., Sabacky M.J., Bachman G.L., Weinkauff D.J. J. Am. Chem. Soc. 99:1977;5946.
12. Soai K., Niwa S. Chem. Rev. 92:1992;833.
13. Fache F., Schulz E., Tommasino M.L., Lemaire M. Chem. Rev. 100:2000;2159.
14. Ager D., Prakash I., Schaad D.R. Chem. Rev. 96:1996;835.
15. Deloux S. Chem. Rev. 93:1993;763.
16. Ghosh A.K., Fidanze S., Senanayake C.H. Synthesis. 1998;937.
17. Qixian, L. 'Songzhi Jiagong Gongyi' (Chinese), China Forestry Publication, 1998; pp. 49-51.
18. Compound 1: Ader, U.; Schneider, M. P. Tetrahedron: Asymmetry 1992, 2, 205. Compounds 2, 4 and 5: Dictionary of Organic Compounds, 6th ed.; Chapman & Hall: London, 1996. Compound 3: Enantiomeric Resolution Procedures for Chemical Compounds, Vol. 1; Newman, P., Ed.; Manhattan College: Riverdale, New York. Compounds 3 and 5: Aldrich Catalog, 2000-2001.
19. Takada H., Takagi S., Kawakubo H. Bull. Chem. Soc. Jpn. 67:1994;1196.
20. For examples: (a) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063; (b) Hosoya, N.; Irie, R.; Katsuki, T. Synlett 1993, 261; (c) Imagawa, K.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1994, 527.
21. For examples: (a) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063; (b) Hosoya, N.; Irie, R.; Katsuki, T. Synlett 1993, 261; (c) Imagawa, K.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1994, 527.
22. For examples: (a) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063; (b) Hosoya, N.; Irie, R.; Katsuki, T. Synlett 1993, 261; (c) Imagawa, K.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1994, 527.
23. Smith H.E., Neergaard J.R., Burrows E.P., Che F.-M. J. Am. Chem. Soc. 96:1974;2908.
24. Larrow J.F., Jacobsen E.N., Gao Y., Hong Y., Nie X., Zepp C.M. J. Org. Chem. 59:1994;1939.