Asymmetric conjugate addition of thiols to a 3-(2-alkenoyl)-2- oxazolidinone catalyzed by the DBFOX/Ph aqua complex of nickel(II) perchlorate [16]

Journal of the American Chemical Society

Volumn 121, Issue 37, 1999, Pages 8675-8676

  Kanemasa, Shuji ^a   Oderaotoshi, Yoji ^a   Wada, Eiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NICKEL COMPLEX; OXAZOLIDINONE DERIVATIVE; OXAZOLINE DERIVATIVE; PERCHLORATE; THIOL DERIVATIVE;

CATALYSIS; CATALYST; COMPLEX FORMATION; CONJUGATION; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033595562     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991064g     Document Type: Letter

References (25)

1. (a) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454-6455.
2. (b) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-I.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074-3088.
3. (c) Kanemasa, S.; Oderaotoshi, Y. J. Synth. Org. Chem. Jpn. 1998, 368-376.
4. (d) Kanemasa, S.; Oderaotoshi, Y.; Tanaka, J.; Wada, E. Tetrahedron Lett. 1998, 39, 7521-7524.
5. Kanemasa, S.; Oderaotoshi, Y.; Tanaka, J.; Wada, E. J. Am. Chem. Soc. 1998, 120, 12355-12356.
6. (a) The Chemistry of the Thiol Group; Patai, S., Ed.; Wiley: New York, 1974.
7. (b) Ohno, A.; Oae, S. In Organic Chemistry of Sulfur, Oae, S., Ed.; Plenum: New York, 1976.
8. (c) Sulphur, Selenium, Silicon, Boron, Organo̊ metallic Compounds; Jones, D. N., Ed.; In Comprehensive Organic Chemistry, The Synthesis and Reactions of Organic Compounds; Barton, D., Ollis, W. D., Series Eds.; Pergamon Press: Oxford, 1979; Vol. 3, pp 3-20.
9. Diastereoselective asymmetric conjugate additions of thiols: (a) Koot, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron: Asymm. 1993, 4, 1941-1948. (b) Wu, M.-J.; Wu, C.-C.; Tseng, T.-C. J. Org. Chem. 1994, 59, 7188-7189. (c) Tseng, T.-C.; Wu, M.-J. Tetrahedron: Asymm. 1995, 6, 1633-1640. (d) Tomioka, K.; Muraoka, A.; Kanai, M. J. Org. Chem. 1995, 60, 6188-6190. (e) Schuurman, R. J. W.; Grimbergen, R. F. P.; Scheeren, H. W.; Nolte, R. J. M. Recl. Trav. Chim. Pays-Bas 1996, 115, 357-362. (f) Miyata, O.; Shinada, T.; Ninomiya, I.; Naito, T. Tetrahedron 1997, 53, 2421-2438.
10. Diastereoselective asymmetric conjugate additions of thiols: (a) Koot, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron: Asymm. 1993, 4, 1941-1948. (b) Wu, M.-J.; Wu, C.-C.; Tseng, T.-C. J. Org. Chem. 1994, 59, 7188-7189. (c) Tseng, T.-C.; Wu, M.-J. Tetrahedron: Asymm. 1995, 6, 1633-1640. (d) Tomioka, K.; Muraoka, A.; Kanai, M. J. Org. Chem. 1995, 60, 6188-6190. (e) Schuurman, R. J. W.; Grimbergen, R. F. P.; Scheeren, H. W.; Nolte, R. J. M. Recl. Trav. Chim. Pays-Bas 1996, 115, 357-362. (f) Miyata, O.; Shinada, T.; Ninomiya, I.; Naito, T. Tetrahedron 1997, 53, 2421-2438.
11. Diastereoselective asymmetric conjugate additions of thiols: (a) Koot, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron: Asymm. 1993, 4, 1941-1948. (b) Wu, M.-J.; Wu, C.-C.; Tseng, T.-C. J. Org. Chem. 1994, 59, 7188-7189. (c) Tseng, T.-C.; Wu, M.-J. Tetrahedron: Asymm. 1995, 6, 1633-1640. (d) Tomioka, K.; Muraoka, A.; Kanai, M. J. Org. Chem. 1995, 60, 6188-6190. (e) Schuurman, R. J. W.; Grimbergen, R. F. P.; Scheeren, H. W.; Nolte, R. J. M. Recl. Trav. Chim. Pays-Bas 1996, 115, 357-362. (f) Miyata, O.; Shinada, T.; Ninomiya, I.; Naito, T. Tetrahedron 1997, 53, 2421-2438.
12. Diastereoselective asymmetric conjugate additions of thiols: (a) Koot, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron: Asymm. 1993, 4, 1941-1948. (b) Wu, M.-J.; Wu, C.-C.; Tseng, T.-C. J. Org. Chem. 1994, 59, 7188-7189. (c) Tseng, T.-C.; Wu, M.-J. Tetrahedron: Asymm. 1995, 6, 1633-1640. (d) Tomioka, K.; Muraoka, A.; Kanai, M. J. Org. Chem. 1995, 60, 6188-6190. (e) Schuurman, R. J. W.; Grimbergen, R. F. P.; Scheeren, H. W.; Nolte, R. J. M. Recl. Trav. Chim. Pays-Bas 1996, 115, 357-362. (f) Miyata, O.; Shinada, T.; Ninomiya, I.; Naito, T. Tetrahedron 1997, 53, 2421-2438.
13. Diastereoselective asymmetric conjugate additions of thiols: (a) Koot, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron: Asymm. 1993, 4, 1941-1948. (b) Wu, M.-J.; Wu, C.-C.; Tseng, T.-C. J. Org. Chem. 1994, 59, 7188-7189. (c) Tseng, T.-C.; Wu, M.-J. Tetrahedron: Asymm. 1995, 6, 1633-1640. (d) Tomioka, K.; Muraoka, A.; Kanai, M. J. Org. Chem. 1995, 60, 6188-6190. (e) Schuurman, R. J. W.; Grimbergen, R. F. P.; Scheeren, H. W.; Nolte, R. J. M. Recl. Trav. Chim. Pays-Bas 1996, 115, 357-362. (f) Miyata, O.; Shinada, T.; Ninomiya, I.; Naito, T. Tetrahedron 1997, 53, 2421-2438.
14. Diastereoselective asymmetric conjugate additions of thiols: (a) Koot, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron: Asymm. 1993, 4, 1941-1948. (b) Wu, M.-J.; Wu, C.-C.; Tseng, T.-C. J. Org. Chem. 1994, 59, 7188-7189. (c) Tseng, T.-C.; Wu, M.-J. Tetrahedron: Asymm. 1995, 6, 1633-1640. (d) Tomioka, K.; Muraoka, A.; Kanai, M. J. Org. Chem. 1995, 60, 6188-6190. (e) Schuurman, R. J. W.; Grimbergen, R. F. P.; Scheeren, H. W.; Nolte, R. J. M. Recl. Trav. Chim. Pays-Bas 1996, 115, 357-362. (f) Miyata, O.; Shinada, T.; Ninomiya, I.; Naito, T. Tetrahedron 1997, 53, 2421-2438.
15. (a) Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417-430.
16. (b) Suzuki, K.; Ikegawa, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1982, 55, 3277-3282.
17. (c) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 363-366.
18. Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975.
19. Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044.
20. Chiral HPLC was performed on a column packed with Daicel chiralcel OD-H with hexane/2-PrOH (9:1 v/v).
21. 8
22. 4 (20 mol %).
23. Treatment of thiol la with the catalyst R,R-A in dichloromethane or diethyl ether immediately precipitated a brown solid which was an active catalyst (see ref 12). Because of the lower solubility of this thiol complex, the reaction in dichloromethane or diethyl ether is less effective, leading to low yields and enantioselectivities.
24. The solid slowly liberates thiol at room temperature.
25. This complex was negative and positive in the halogen and sulfer tests, respectively, and no liberation of thiol Ia was detected. Although it is soluble in acetone, THF, and dichloromethane, no catalytic activity was observed in the thiol conjugate addition.