Enantioselective Michael reaction catalyzed by well-defined chiral Ru amido complexes: Isolation and characterization of the catalyst intermediate, Ru malonato complex having a metal-carbon bond

Journal of the American Chemical Society

Volumn 125, Issue 25, 2003, Pages 7508-7509

  Watanabe, Masahito ^a   Murata, Kunihiko ^a   Ikariya, Takao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOACETIC ACID; CARBON; MALONIC ACID; METAL; RUTHENIUM AMIDE COMPLEX; RUTHENIUM COMPLEX; RUTHENIUM MALONATE COMPLEX; RUTHENIUM[N (4 TOLUENESULFONYL) 1,2 DIPHENYLETHYLENEDIAMINE]; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHIRALITY; ENANTIOSELECTIVITY; ISOLATION PROCEDURE; MICHAEL ADDITION; STEREOCHEMISTRY;

EID: 0037870594     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035435b     Document Type: Article

References (21)

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6. Recent leading reviews on chiral metal catalyzed reaction: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999; Vol. 3, pp 1105-1139. (b) Krause, N.; Hoffman-Röder, A. Synthesis 2001, 171-196. (c) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033-8061. [Cu] (d) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. [Rh] (e) Hayashi, T. Synlett 2001, 879-887. [Ln] (f) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2209. A practical ALB catalyst: (g) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Agew. Chem., Int. Ed. Engl. 1996, 35, 104-106. (h) Arai, T.; Yamada, Y.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368-1372.
7. Recent leading reviews on chiral metal catalyzed reaction: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999; Vol. 3, pp 1105-1139. (b) Krause, N.; Hoffman-Röder, A. Synthesis 2001, 171-196. (c) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033-8061. [Cu] (d) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. [Rh] (e) Hayashi, T. Synlett 2001, 879-887. [Ln] (f) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2209. A practical ALB catalyst: (g) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Agew. Chem., Int. Ed. Engl. 1996, 35, 104-106. (h) Arai, T.; Yamada, Y.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368-1372.
8. Recent leading reviews on chiral metal catalyzed reaction: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999; Vol. 3, pp 1105-1139. (b) Krause, N.; Hoffman-Röder, A. Synthesis 2001, 171-196. (c) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033-8061. [Cu] (d) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. [Rh] (e) Hayashi, T. Synlett 2001, 879-887. [Ln] (f) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2209. A practical ALB catalyst: (g) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Agew. Chem., Int. Ed. Engl. 1996, 35, 104-106. (h) Arai, T.; Yamada, Y.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368-1372.
9. Recent leading reviews on chiral metal catalyzed reaction: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999; Vol. 3, pp 1105-1139. (b) Krause, N.; Hoffman-Röder, A. Synthesis 2001, 171-196. (c) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033-8061. [Cu] (d) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. [Rh] (e) Hayashi, T. Synlett 2001, 879-887. [Ln] (f) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2209. A practical ALB catalyst: (g) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Agew. Chem., Int. Ed. Engl. 1996, 35, 104-106. (h) Arai, T.; Yamada, Y.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368-1372.
10. Recent leading reviews on chiral metal catalyzed reaction: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999; Vol. 3, pp 1105-1139. (b) Krause, N.; Hoffman-Röder, A. Synthesis 2001, 171-196. (c) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033-8061. [Cu] (d) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. [Rh] (e) Hayashi, T. Synlett 2001, 879-887. [Ln] (f) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2209. A practical ALB catalyst: (g) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Agew. Chem., Int. Ed. Engl. 1996, 35, 104-106. (h) Arai, T.; Yamada, Y.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368-1372.
11. Recent leading reviews on chiral metal catalyzed reaction: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999; Vol. 3, pp 1105-1139. (b) Krause, N.; Hoffman-Röder, A. Synthesis 2001, 171-196. (c) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033-8061. [Cu] (d) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. [Rh] (e) Hayashi, T. Synlett 2001, 879-887. [Ln] (f) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2209. A practical ALB catalyst: (g) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Agew. Chem., Int. Ed. Engl. 1996, 35, 104-106. (h) Arai, T.; Yamada, Y.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368-1372.
12. Recent leading reviews on chiral metal catalyzed reaction: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999; Vol. 3, pp 1105-1139. (b) Krause, N.; Hoffman-Röder, A. Synthesis 2001, 171-196. (c) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033-8061. [Cu] (d) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. [Rh] (e) Hayashi, T. Synlett 2001, 879-887. [Ln] (f) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2209. A practical ALB catalyst: (g) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Agew. Chem., Int. Ed. Engl. 1996, 35, 104-106. (h) Arai, T.; Yamada, Y.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368-1372.
13. Recent leading reviews on chiral metal catalyzed reaction: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999; Vol. 3, pp 1105-1139. (b) Krause, N.; Hoffman-Röder, A. Synthesis 2001, 171-196. (c) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033-8061. [Cu] (d) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. [Rh] (e) Hayashi, T. Synlett 2001, 879-887. [Ln] (f) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2209. A practical ALB catalyst: (g) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Agew. Chem., Int. Ed. Engl. 1996, 35, 104-106. (h) Arai, T.; Yamada, Y.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368-1372.
14. The catalysts 1c-e were found to be deactivated during the reaction at a higher temperature of 40-60 °C, leading to pale yellow crystalline complexes, which were structurally determined to be new type of Ru complexes bearing an M-C bond by X-ray crystallographic analysis. A detailed structure and formation mechanism will be reported in a separate paper.
15. For the mechanism of a Michael type reaction catalyzed by chiral transition metal complexes, see: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052-5058. (b) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241. (c) Michael reaction of 1-oxoindanecarboxylate and methyl vinyl ketone with chiral Rh amido complexes was reported independently by Suzuki et al. Suzuki, T.; Torii, T. Tetrahedron: Asymmetry 2001, 12, 1077-1081.
16. For the mechanism of a Michael type reaction catalyzed by chiral transition metal complexes, see: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052-5058. (b) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241. (c) Michael reaction of 1-oxoindanecarboxylate and methyl vinyl ketone with chiral Rh amido complexes was reported independently by Suzuki et al. Suzuki, T.; Torii, T. Tetrahedron: Asymmetry 2001, 12, 1077-1081.
17. For the mechanism of a Michael type reaction catalyzed by chiral transition metal complexes, see: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052-5058. (b) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241. (c) Michael reaction of 1-oxoindanecarboxylate and methyl vinyl ketone with chiral Rh amido complexes was reported independently by Suzuki et al. Suzuki, T.; Torii, T. Tetrahedron: Asymmetry 2001, 12, 1077-1081.
18. 2 = 0. See Supporting Information.
19. Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571-1572.
20. Recently, Hartwig reported that an isolable C-bound aryl malonato Pd complex gave the reductive elimination product, 2-aryl-1,3-diketone. Wolkowski, J. P.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4289-4291.
21. The reaction of 1.07 g of 2a and 1.72 g of 3a in tert-butyl alcohol containing 72 mg of the catalyst If gave 2.76 g of the Michael adduct with 98% ee and in 99% yield.