Kinetic resolution of axially chiral 2,2′-dihydroxy-1,1′- biaryls by palladium-catalyzed alcoholysis

Journal of the American Chemical Society

Volumn 127, Issue 30, 2005, Pages 10474-10475

  Aoyama, Hiroshi ^a   Tokunaga, Makoto ^a   Kiyosu, Junya ^a   Iwasawa, Tetsuo ^a   Obora, Yasushi ^a   Tsuji, Yasushi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYL GROUP; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ALCOHOLYSIS; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHIRALITY; HYDROLYSIS; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 23044507662     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051750h     Document Type: Article

References (24)

1. (a) Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008-2022 and references therein,
2. (b) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525-558 and references therein,
3. (c) Habaue, S.; Seko, T.; Okamoto, Y. Macromolecules 2003, 36, 2604-2608.
4. Telfer, S. G.; Kuroda, R. Coord. Chem. Rev. 2003, 242, 33-46.
5. For example: (a) Lin, G.-Q.; Zhong, M. Tetrahedron Lett. 1997, 38, 1087-1090.
6. (b) Toda, F.; Tanaka, K.; Miyamoto, H.; Koshima, H.; Miyahara, I.; Hirotsu, K. J. Chem. Soc., Perkin Trans. 2 1997, 1877-1885.
7. (c) Delogu, G.; Fabbri, D.; Dettori, M. A.; Forni, A.; Casalone, G. Tetrahedron: Asymmetry 2000, 11, 4417-4427.
8. (d) Meyers, A. I.; Nelson, T. D.; Moorlag, H.; Rawson, D. J.; Meier, A. Tetrahedron 2004, 60, 4459-4473.
9. (e) Brunel, J. M. Chem. Rev. 2005, 105, 857-897.
10. (a) Irie, R.; Masutani, K.; Katsuki, T. Synlett 2000, 1433-1436.
11. (b) Barhate, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529-2532.
12. (c) Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Angew. Chem., Int. Ed. 2002, 41, 4532-4535.
13. (d) Li, X.; Hewgley, B.; Mulrooney, C. A.; Yang, J.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 5500-5511.
14. (e) Somei, H.; Asano, Y.; Yoshida, T.; Takizawa, S.; Yamataka, H.; Sasai, H. Tetrahedron Lett. 2004, 45, 1841-1844.
15. HKR of epoxides: (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936-938.
16. (b) Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307-1315.
17. (c) Nielsen, L. P. C.; Stevenson, C. P.; Blackmond, D. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360-1362.
18. Aoyama, H.; Tokunaga, M.; Hiraiwa, S.; Shirogane, Y.; Obora, Y.; Tsuji, Y. Org. Lett. 2004, 6, 509-512.
19. Examples of methanolysis: (a) Liang, J.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1998, 63, 3154-3155.
20. (b) Tanaka, S.; Saburi, H.; Ishibashi, Y.; Kitamura, M. Org. Lett. 2004, 6, 1873-1875.
21. Watson, M. D.; Fechtenkotter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267-1300 and references therein.
22. Iwasawa, T.; Tokunaga, M.; Obora, Y.; Tsuji, Y. J. Am. Chem. Soc. 2004, 126, 6554-6555.
23. Bosch, M.; Schlaf, M. J. Org. Chem. 2003, 68, 5225-5227.
24. rel values were calculated as a first-order reaction from both 1 and 2, then the lower value was taken.