Asymmetric sulfimidation with cis-β Ru(salalen)CO2 complexes as catalyst

Chemistry Letters

Volumn 36, Issue 9, 2007, Pages 1092-1093

  Fujita, Hidekazu ^a   Uchida, Tatsuya ^a   Irie, Ryo ^a,b   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34948882688     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.1092     Document Type: Article

References (26)

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4. For asymmetric reactions with cis-β M(salen) complexes, see: a) Y. N. Belokon', B. Green, N. S. Ikonnikov, V. S. Larichev, B. V. Lokshin, M. A. Moscalenko, M. North, C. Orizu, A. S. Peregudov, G. I. Timofeeva, Eur. J. Org. Chem. 2000, 2655.
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11. For asymmetric reactions with cis-β M(salalen) complexes, see: a) K. Matsumoto, Y. Sawada, B. Saito, K. Sakai, T. Katsuki, Angew. Chem., Int. Ed. 2005, 44, 4935.
12. b) Y. Sawada, K. Matsumoto, T. Katsuki, Angew. Chem., Int. Ed. 2007, 46, 4559.
13. c) T. Yamaguchi, K. Matsumoto, T. Katsuki, Angew. Chem., Int. Ed. 2007, 46, 4729.
14. d) B. Saito, T. Katsuki, Angew. Chem., Int. Ed. 2005, 44, 4600.
15. For asymmetric epoxidation with a cis-β M(salan) complex, see: Y. Sawada, K. Matsumoto, S. Kondo, H. Watanabe, T. Ozawa, K. Suzuki, B. Saito, T. Katsuki, Angew. Chem., Int. Ed. 2006, 45, 3478.
16. Achiral titanium and zirconium(salalen) complexes have been prepared: A. Yeori, S. Gendler, S. Groysman, I. Goldberg, M. Kol, Inorg. Chem. Commun. 2004, 7, 280.
17. For a review on asymmetric sulfimidation using [N-(p-ary1- sulfonyl)imino]phenyliodinane as the nitrene precursor, see: P. C. Taylor, in Sulfur Reports 1999, Vol. 21, p. 241.
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19. b) M. Murakami, T. Uchida, B. Saito, T. Katsuki, Chirality 2003, 15, 116.
20. 2 complex has also been reported to adopt a cis-β configuration, due to the trans-effect of the CO ligand: W.-H. Leung, E. Y. Y. Chan, E. K. F. Chow, I. D. Williams, S.-M. Peng, J. Chem. Soc., Dalton Trans. 1996, 1229.
21. a) A. A. Purwoko, S. D. Tibensky, A. J. Lees, Inorg. Chem. 1996, 35, 7049.
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23. c) N. A. Bokach, M. Haukka, P. Hirva, M. F. C. G. Da Silva, V. Y. Kukushkin, A. J. L. Pombeiro, J. Orgnometal. Chem. 2006, 691, 2368.
24. 4(o-OMe) was also sluggish. These results indicate that the electronic effect of the o-substituent is not responsible for low reactivity of o-substituted aryl methyl sulfides.
25. For examples, the reactions of ethyl phenyl sulfide and n-decyl methyl sulfide for 24 h gave the corresponding sulfimides of 50 and 48% ees in 12 and 24% yields, respectively.
26. CCDC 651311 and 651312 (for complexes 1 and 7) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.