Chiral 2,2-disubstituted cyclopropanecarboxylic acids: Effective derivatizing agents for analysis of enantiomeric purity of alcohols and for resolution of 1,1'-Bi-2-naphthol

Tetrahedron Letters

Volumn 38, Issue 22, 1997, Pages 3959-3962

  Kim, Hyun Chang ^a   Choi, Soojin ^a   Kim, Hongdoo ^a   Ahn, Kwang Hyun ^a   Koh, Jeong Hwan ^b   Park, Jaiwook ^b  

^a Kyung Hee University   (South Korea)

^b Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHOL; 2,2' DIHYDROXY 1,1' BINAPHTHYL; ALCOHOL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0031005106     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00789-2     Document Type: Article

References (21)

1. Morrison, J. D. Asymmetric Synthesis, Academic Press, New York 1983, Vol. I.
2. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1968, 90, 3732-3738.
3. (b) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
4. (c) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
5. (d) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143-2147.
6. Tottie, L.; Moberg, C.; Heuman, A. Acta Chem. Sca, 1993, 47, 492-499.
7. Latypov, S. K.; Seco, J. M.; Quiñoá, E.; Riguera, R. J. Org. Chem. 1995, 60, 1538-1545 and references therein.
8. (a) Takeuchi, Y.; Itoh, N.; Note, H.; Koizumi, T.; Yamaguchi, K. J. Am. Chem. Soc. 1991, 113, 6318-6320.
9. (b) Alexakis, A.; Mutti, S.; Mangeney, P. J. Org. Chem. 1992, 57, 1224-1237.
10. (c) Silks, L. A.; Peng, J.; Odom, J. D.; Dunlap, R. B. J. Org. Chem. 1991, 56, 6733-6736.
11. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728.
12. 3): δ 7.35-7.17 (m, 10H), 2.50 (dd, 1H, J=8.4Hz, 6.3Hz), 2.11 (dd, 1H, J=6.3Hz, 5.0Hz), 1.66 (dd, 1H, J=8.4Hz, 5.0Hz).
13. Ward, D. E.; Rhee, C. K. Tetrahedron Lett. 1991, 32, 7165-7166.
14. Neises, B.; Steglich, W. Org. Synth., Coll. Vol. VII 1990, 93-95.
15. (a) Chow, H. -F.; Wan, C. -W.; Ng, M. -K. J. Org. Chem. 1996, 61, 8712-8714.
16. (b) Cai, D.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7991-7994.
17. (c) Hu, Q. -S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123-2126.
18. For reviews, see: (a) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021-1050.
19. (b) Singh, V. K. Synthesis 1992, 605-617.
20. (c) Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503-517.
21. 1H NMR, of which stereochemistry was confirmed by comparison with the authentic sample prepared from (R)-binol and (S)-1a.