Facile synthesis of C2-symmetric chiral binaphthyl ketone catalysts

Tetrahedron Letters

Volumn 41, Issue 13, 2000, Pages 2149-2152

  Seki, Masahiko ^a   Furutani, Toshiyuki ^a   Hatsuda, Masanori ^a   Imashiro, Ritsuo ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

Biaryls; Enzymes and enzyme reactions; Epoxidation; Ullmann reactions

Indexed keywords

BINAPHTHYL ACETATE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; ENANTIOMER; EPOXIDATION; HYDROLYSIS; REACTION ANALYSIS; SYNTHESIS;

EID: 0034719897     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00120-9     Document Type: Article

References (20)

1. (a) Murray, R. W. Chem. Rev. 1989, 89, 1187.
2. (b) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806.
3. (c) Denmark, S. E.; Wu, Z. Synlett 1999, 847.
4. (a) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1996, 118, 491.
5. (b) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11 311.
6. (c) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
7. (a) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242.
8. (b) Kanoh, S.; Hongoh, Y.; Motoi, M.; Suda, H. Bull. Chem. Soc. Jpn. 1988, 61, 1032.
9. (a) Zlatanos, S. N.; Sagredos, A. N. J. Am. Oil Chem. Soc. 1990, 67, 661.
10. (a) Zlatanos, S. N.; Sagredos, A. N. J. Am. Oil Chem. Soc. 1990, 67, 661. (b) Ikeda, I.; Gu, X.-P.; Miyamoto, I.; Okahara, M. J. Am. Oil Chem. Soc. 1989, 66, 822.
11. The copper powder (particle size: 100-200 mesh) was purchased from Kanto Chemicals Co., Inc. and used without further purification.
12. 2O (95%)].
13. Smith, J. G.; Dibble, P. W.; Sandborn, R. E. J. Org. Chem. 1986, 51, 3762.
14. Enzymatic kinetic resolution of 2,2′-dihydroxy-1,1′-binaphthyl was reported: (a) Kazlauskas, R. J. J. Am. Chem. Soc. 1989, 111, 4953.
15. (b) Inagaki, M.; Hiratake, J.; Nishioka, T.; Oda, J. Agric. Biol. Chem. 1989, 53, 1879.
16. The e.e.s of the products were determined by HPLC: Chiralcel OD (Daicel), n-hexane:2-propanol=10:1, 1 mL/min, 40°C, 224 nm.
17. 2a,b HPLC: Chiralcel OD (Daicel), n-hexane:2-propanol=10:1, 1 mL/min, 40°C, 224 nm.
18. 3).
19. 2b While the yield of the cyclization is moderate (60% yield), that of the oxidation step is poor (21% yield).
20. 3).