Cinchona alkaloid/sulfinyl chloride combinations: Enantioselective sulfinylating agents of alcohols

Journal of the American Chemical Society

Volumn 127, Issue 5, 2005, Pages 1374-1375

  Shibata, Norio ^a   Matsunaga, Mitsuharu ^a   Nakagawa, Masaya ^a   Fukuzumi, Takeo ^a   Nakamura, Shuichi ^a   Toru, Takeshi ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ARENESULFINATE; CHLORIDE; CINCHONA ALKALOID; SULFINIC ACID DERIVATIVE; SULFINYL CHLORIDE; TERT BUTYL 4 TOLUENESULFINATE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SULFINYLATION;

ALCOHOLS; CINCHONA ALKALOIDS; STEREOISOMERISM; SULFINIC ACIDS;

EID: 13444310562     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0430189     Document Type: Article

References (29)

1. (a) Mikolajczk, M.; Drabowicz, J.; Kielbasinski, P. Chiral Sulfur Reagents; CRC Press: Boca Raton, FL, 1997.
2. (b) Carreno, M. C. Chem. Rev. 1995, 95, 1717.
3. (c) Toru, T.; Nakamura, S. J. Synth. Org. Chem. Jpn. 2002, 60, 115.
4. (d) Nakamura, S.; Watanabe, Y.; Toru, T. J. Org. Chem. 2000, 65, 1758.
5. (e) Khiar, N.; Fernández, I.; Alcudia, A.; Alcudia, F. In Advances in Sulfur Chemistry 2; Rayner, C. M., Ed.; JAI Press: Stamford, CT, 2000; Chapter 3.
6. (f) Matsugi, M.; Shibata, N.; Kita, Y. In Advances in Sulfur Chemistry 2; Rayner, C. M., Ed.; JAI Press: Stamford, CT, 2000; Chapter 6.
7. (a) Phillips, H. J. Chem. Soc. 1925, 127, 2552.
8. (b) Fernández, I.; Khiar, N.; Liera, J. M.; Alcudia, F. J. Org. Chem. 1992, 57, 6789.
9. (c) Fernández, I.; Khiar, N.; Roca, A.; Benabra, A.; Alcudia, A.; Espartero, J. L.; Alcudia, F. Tetrahedron Lett. 1999, 40, 2029.
10. (d) Khiar, N.; Araújo, C. S.; Alcudia, F.; Fernández, I. J. Org. Chem. 2002, 67, 345.
11. (e) Alayrac, C.; Nowaczyk, S.; Lemarié, M.; Metzner, P. Synthesis 1999, 669.
12. (f) Whitesell, J. K.; Wong, M. S. J. Org. Chem. 1991, 56, 4552.
13. (g) Whitesell, J. K.; Wong, M. S. J. Org. Chem. 1994, 59, 597.
14. (h) Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794.
15. (i) Watanabe, Y.; Mase, N.; Tateyama, M.; Toru, T. Tetrahedron: Asymmetry 1999, 10, 737.
16. (a) Drabowicz, J.; Lagedz, S.; Mikolajczyk, M. Tetrahedron 1988, 44, 5243.
17. (b) Drabowicz, J.; Legedz, S.; Mikolajczyk, M. J. Chem. Soc., Chem. Commun. 1985, 1670.
18. (c) Mikolajczyk, M.; Drabowicz, J. J. Chem. Soc., Chem. Commun. 1974, 547.
19. (d) Evans, J. W.; Fierman, M. B.; Miller, S. J.; Ellman, J. A. J. Am. Chem. Soc. 2004, 126, 8134.
20. (a) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728.
21. (b) Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M. J. Am. Chem. Soc. 2001, 123, 7001.
22. (c) Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K. L. J. Org. Chem. 2003, 68, 2494.
23. (d) Shibata, N.; Ishimaru, T.; Nakamura, M.; Toru, T. Synlett 2004, 2509.
24. (a) Youn, J. H.; Herrmann, R. Tetrahedron Lett. 1985, 27, 1493.
25. (b) Peyronneau, M.; Roques, N.; Mazieres, S.; Roux, C. L. Synlett 2003, 631.
26. (a) Busu, A.; Gallagher, D. J.; Beak, P. J. Org. Chem. 1996, 61, 5718.
27. (b) Khiar, N.; Araújo, S. S.; Alcudia, F.; Fernández, I. J. Org. Chem. 2002, 67, 345.
28. (c) Balcells, D.; Maseras, F.; Khiar, N. Org. Lett. 2004, 6, 2197.
29. (d) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn, 1995, 68, 36.