Cinchona alkaloid-sulfinyl chloride combinations: Catalytic enantioselective sulfinylation of alcohols

Synlett

Volumn , Issue 11, 2005, Pages 1699-1702

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

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Alcohols; Alkaloids; Asymmetric catalyst; Asymmetric synthesis; Sulfoxides

Indexed keywords

ALCOHOL; CHLORIDE; CINCHONA ALKALOID; SULFINYL CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SULFINYLATION; SYNTHESIS;

EID: 22244482761     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871535     Document Type: Article

References (29)

1. (a) Mikolajczk, M.; Drabowicz, J.; Kielbasinski, P. Chiral Sulfur Reagents; CRC Press: Boca Raton, 1997.
2. (b) Carreño, M. C. Chem. Rev. 1995, 95, 1717.
3. (c) Toru, T.; Nakamura, S. J. Synth. Org. Chem. Jpn. 2002, 50, 115.
4. (d) Khiar, N.; Fernández, I.; Alcudia, A.; Alcudia, F. In Advances in Sulfur Chemistry, 2nd ed.; Rayner, C. M., Ed.; JAI Press: Stamford, 2000, Chap. 3.
5. (e) Fernández, I.; Khiar, N. Chem. Rev. 2003, 103, 3651.
6. (a) Drabowicz, J.; Lagedź, S.; Mikolajczyk, M. Tetrahedron 1988, 44, 5243.
7. (b) Drabowicz, J.; Legedź, S.; Mikołajczyk, M. J. Chem. Soc., Chem. Commun. 1985, 1670.
8. (c) Mikołajczyk, M.; Drabowicz, J. J. Chem. Soc., Chem. Commun. 1974, 547.
9. (d) Evans, J. W.; Fierman, M. B.; Miller, S. J.; Ellman, J. A. J. Am. Chem. Soc. 2004, 126, 8134.
10. (e) Nakamura, S.; Tateyama, M.; Sugimoto, H.; Nakagawa, M.; Watanabe, Y.; Shibata, N.; Toru, T. Chirality 2005, 17, 85.
11. (a) Phillips, H. J. Chem. Soc. 1925, 127, 2552.
12. (b) Fernández, I.; Khiar, N.; Llera, J. M.; Alcudia, F. J. Org. Chem. 1992, 57, 6789.
13. (c) Fernández, I.; Khiar, N.; Roca, A.; Benabra, A.; Alcudia, A.; Espartero, J. L.; Alcudia, F. Tetrahedron Lett. 1999, 40, 2029.
14. (d) Khiar, N.; Araújo, C. S.; Alcudia, F.; Fernández, I. J. Org. Chem. 2002, 67, 345.
15. (e) Alayrac, C.; Nowaczyk, S.; Lemarié, M.; Metzner, P. Synthesis 1999, 669.
16. (f) Whitesell, J. K.; Wong, M. S. J. Org. Chem. 1991, 56, 4552.
17. (g) Whitesell, J. K.; Wong, M. S. J. Org. Chem. 1994, 59, 597.
18. (h) Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794.
19. (i) Watanabe, Y.; Mase, N.; Tateyama, M.; Toru, T. Tetrahedron: Asymmetry 1999, 10, 737.
20. (j) Khiar, N.; Alcudia, F.; Espartero, J.-L.; Rodríguez, L.; Fernández, I. J. Am. Chem. Soc. 2000, 122, 7598.
21. (k) Lu, B. Z.; Jin, F.; Zhang, Y.; Wu, X.; Wald, S. A.; Senanayake, C. H. Org. Lett. 2005, 7, 1465.
22. Shibata, N.; Matunaga, M.; Nakagawa, M.; Fukuzumi, T.; Nakamura, S.; Toru, T. J. Am. Chem. Soc. 2005, 127, 1374.
23. (a) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728.
24. (b) Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M. J. Am. Chem. Soc. 2001, 123, 7001.
25. (c) Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K. L. J. Org. Chem. 2003, 68, 2494.
26. (d) Shibata, N.; Ishimaru, T.; Nakamura, S.; Toru, T. Synlett 2004, 2509.
27. 4. The solution was evaporated under reduced pressure to give crude sulfinate, which was purified by column chromatography (silica 25 g, EtOAc-hexane = 1:9) to give 3b (54 mg, 90%, 94% ee).
28. Just before the submission of the manuscript, a catalytic enantioselective sulfinyl transfer using cinchona alkaloid catalysts was reported. See: Peltier, H. M.; Evans, J. W.; Ellman, J. A. Org. Lett. 2005, 7, 1733.
29. The catalytic enantioselective sulfinylation of alcohols using arenesulfinyl chlorides instead of alkanesulfinyl chlorides was attempted; however, the enantioselectivities of the arenesulfinates obtained were very low.