A novel method for the synthesis of (R)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid by asymmetric oxidative coupling of a chiral β-naphthol derivative catalyzed by CuCl

Tetrahedron Asymmetry

Volumn 13, Issue 17, 2002, Pages 1937-1940

  Xin, Zhuo qun ^a   Da, Chao shan ^a   Dong, Shou liang ^a   Liu, Da xue ^a   Wei, Jie ^a   Wang, Rui ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3 HYDROXY 2 NAPHTHYLCARBONYL)PYRROLIDINE 2 CARBOXYLIC ACID METHYL ESTER; 1,1' BINAPTHYL 3,3' DICARBOXYLIC ACID; 2,2' DIHYDROXY 1,1' BINAPHTHYL 3,3' DICARBOXYLIC ACID; 2,2' DIHYDROXY 3,3' BIS(2 METHOXYCARBONYL 1 PYRROLIDINYLCARBONYL) 1,1' BINAPHTHALENE; CARBOXYLIC ACID DERIVATIVE; CARBROMAL; COPPER CHLORIDE; NAPHTHALENE DERIVATIVE; NAPHTHOL DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION TIME; SOLVENT EFFECT; SYNTHESIS; TEMPERATURE;

EID: 0037048353     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00507-4     Document Type: Article

References (20)

1. Pu L. Chem. Rev. 98:1998;2405-2494.
2. Pu L., Yu H.B. Chem. Rev. 101:2001;757-824.
3. Yang X.W., Sheng J.H., Da C.S., Wang H.S., Su W., Wang R., Chan A.S.C. J. Org. Chem. 65:2000;295-296.
4. Yang X.W., Su W., Liu D.X., Wang H.S., Shen J.H., Da C.S., Wang R., Chan A.S.C. Tetrahedron. 56:2000;3511-3516.
5. Kitajima H., Ito K., Aoki Y., Katsuki T. Bull. Chem. Soc. Jpn. 70:1997;207-217.
6. Casas J., Nájera C., Sansano J.M., González J., Saá J.M., Vega M. Tetrahedron: Asymmetry. 12:2001;699-702.
7. Brussee J., Jansen A.C.A. Tetrahedron Lett. 24:1983;3261-3261.
8. Brussee J., Groenendijk J.L.G., te Koppele J.M., Jansen A.C.A. Tetrahedron. 41:1985;3313-3319.
9. Smrčina M., Lorenc M., Hanuš V., Sedmera P., Kočovský P. J. Org. Chem. 57:1992;1917-1920.
10. Smrčina M., Poláková J., Vyskočil Š., Kočovský P. J. Org. Chem. 58:1993;4534-4538.
11. Hon S.W., Li C.H., Kuo J.H., Barhate N.B., Liu Y.H., Wang Y., Chen C.T. Org. Lett. 3:2001;869-872.
12. Li X.L., Yang J., Kozlowski M.C. Org. Lett. 3:2001;1137-1140.
13. Barhate N.B., Chen C.T. Org. Lett. 4:2002;2529-2532.
14. Cram D.J., Helgeson R.C., Peacock S.C., Kaplan L.J., Domeier L.A., Moreau P., Koga K., Mayer J.M., Chao Y., Siegel M.G., Hoffman D.H., Sogah G.D.Y. J. Org. Chem. 43:1978;1930-1946.
15. Nakajima M., Miyoshi I., Kanayama K., Hashimoto S.I., Noji M., Koga K. J. Org. Chem. 64:1999;2264-2271.
16. Su W., Wang H.S., Da C.S., Wang R. Chem. J. Chin. Univ. 21:2000;1408-1409.
17. Nakajima M., Miyoshi I., Kanayama K., Hashimoto S.I. Tetrahedron Lett. 36:1995;9519-9520.
18. Noji M., Nakajima M., Koga K. Tetrahedron Lett. 35:1994;7983-7984.
19. Reetz M.T., Merk C., Mehler G. Chem. Commun. 1998;2075-2076.
20. Enders D., Kipphardt H., Gerdes P., Brena-Valle L.J., Bhushan V. Bull. Soc. Chim. Belg. 97:1988;691-704.