Transfer hydrogenation of activated C=C bonds catalyzed by ruthenium amido complexes: Reaction scope, limitation, and enantioselectivity

Journal of Organic Chemistry

Volumn 70, Issue 9, 2005, Pages 3584-3591

  Xue, Dong ^a,b   Chen, Ying Chun ^c   Cui, Xin ^a   Wang, Qi Wei ^a   Zhu, Jin ^a   Deng, Jin Gen ^a,b  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c SICHUAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSIS; CHEMICAL BONDS; COMPLEXATION; KETONES; REDUCTION; RUTHENIUM; UNSATURATED COMPOUNDS;

CHEMOSELECTIVITY; CHIRAL; METAL PRECURSORS; TRANSFER HYDROGENATION;

HYDROGENATION;

ALKENE DERIVATIVE; ALPHA,ALPHA DICYANOOLEFIN; DIAMINE RUTHENIUM; RUTHENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; ENANTIOSELECTIVITY; HYDROGENATION; SYNTHESIS;

EID: 17744381791     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0478205     Document Type: Article

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55. For selected reports on other metallic hydride mediated asymmetric conjugate reductions, see: (a) Misun, M.; Pfaltz Helv. Chim. Acta 1996, 79, 961 and references therein. (b) Yamada, T.; Ohtsuka, Y.; Ikeno, T. Chem. Lett. 1998, 1129. (c) Chiu, P.; Szeto, C.-P.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Kamenecha, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (e) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829 and references therein. (f) Jurkauskas V.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 2892 and references therein. (g) Lipshutz, B. H.; Servesko, J. M. Angew. Chem., Int. Ed. 2003, 42, 4789 and references therein. (h) Czekelius, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 4793.
56. For selected reports on other metallic hydride mediated asymmetric conjugate reductions, see: (a) Misun, M.; Pfaltz Helv. Chim. Acta 1996, 79, 961 and references therein. (b) Yamada, T.; Ohtsuka, Y.; Ikeno, T. Chem. Lett. 1998, 1129. (c) Chiu, P.; Szeto, C.-P.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Kamenecha, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (e) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829 and references therein. (f) Jurkauskas V.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 2892 and references therein. (g) Lipshutz, B. H.; Servesko, J. M. Angew. Chem., Int. Ed. 2003, 42, 4789 and references therein. (h) Czekelius, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 4793.
57. For selected reports on other metallic hydride mediated asymmetric conjugate reductions, see: (a) Misun, M.; Pfaltz Helv. Chim. Acta 1996, 79, 961 and references therein. (b) Yamada, T.; Ohtsuka, Y.; Ikeno, T. Chem. Lett. 1998, 1129. (c) Chiu, P.; Szeto, C.-P.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Kamenecha, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (e) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829 and references therein. (f) Jurkauskas V.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 2892 and references therein. (g) Lipshutz, B. H.; Servesko, J. M. Angew. Chem., Int. Ed. 2003, 42, 4789 and references therein. (h) Czekelius, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 4793.
58. For selected reports on other metallic hydride mediated asymmetric conjugate reductions, see: (a) Misun, M.; Pfaltz Helv. Chim. Acta 1996, 79, 961 and references therein. (b) Yamada, T.; Ohtsuka, Y.; Ikeno, T. Chem. Lett. 1998, 1129. (c) Chiu, P.; Szeto, C.-P.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Kamenecha, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (e) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829 and references therein. (f) Jurkauskas V.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 2892 and references therein. (g) Lipshutz, B. H.; Servesko, J. M. Angew. Chem., Int. Ed. 2003, 42, 4789 and references therein. (h) Czekelius, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 4793.
59. For selected reports on other metallic hydride mediated asymmetric conjugate reductions, see: (a) Misun, M.; Pfaltz Helv. Chim. Acta 1996, 79, 961 and references therein. (b) Yamada, T.; Ohtsuka, Y.; Ikeno, T. Chem. Lett. 1998, 1129. (c) Chiu, P.; Szeto, C.-P.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Kamenecha, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (e) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829 and references therein. (f) Jurkauskas V.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 2892 and references therein. (g) Lipshutz, B. H.; Servesko, J. M. Angew. Chem., Int. Ed. 2003, 42, 4789 and references therein. (h) Czekelius, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 4793.
60. For selected reports on other metallic hydride mediated asymmetric conjugate reductions, see: (a) Misun, M.; Pfaltz Helv. Chim. Acta 1996, 79, 961 and references therein. (b) Yamada, T.; Ohtsuka, Y.; Ikeno, T. Chem. Lett. 1998, 1129. (c) Chiu, P.; Szeto, C.-P.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Kamenecha, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (e) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829 and references therein. (f) Jurkauskas V.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 2892 and references therein. (g) Lipshutz, B. H.; Servesko, J. M. Angew. Chem., Int. Ed. 2003, 42, 4789 and references therein. (h) Czekelius, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 4793.
61. For selected reports on other metallic hydride mediated asymmetric conjugate reductions, see: (a) Misun, M.; Pfaltz Helv. Chim. Acta 1996, 79, 961 and references therein. (b) Yamada, T.; Ohtsuka, Y.; Ikeno, T. Chem. Lett. 1998, 1129. (c) Chiu, P.; Szeto, C.-P.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Kamenecha, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (e) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829 and references therein. (f) Jurkauskas V.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 2892 and references therein. (g) Lipshutz, B. H.; Servesko, J. M. Angew. Chem., Int. Ed. 2003, 42, 4789 and references therein. (h) Czekelius, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 4793.
62. For selected reports on other metallic hydride mediated asymmetric conjugate reductions, see: (a) Misun, M.; Pfaltz Helv. Chim. Acta 1996, 79, 961 and references therein. (b) Yamada, T.; Ohtsuka, Y.; Ikeno, T. Chem. Lett. 1998, 1129. (c) Chiu, P.; Szeto, C.-P.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Kamenecha, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (e) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829 and references therein. (f) Jurkauskas V.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 2892 and references therein. (g) Lipshutz, B. H.; Servesko, J. M. Angew. Chem., Int. Ed. 2003, 42, 4789 and references therein. (h) Czekelius, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 4793.
63. For hydride transfer as the key step in the hydrogenation of iminium ion catalyzed by a P-P* ruthenium hydride complex, see: (a) Magee, M. P.; Norton, J. R. J. Am. Chem. Soc. 2001, 123, 1778. (b) Rossen, K. Angew. Chem., Int. Ed. 2001, 40, 4611.
64. For hydride transfer as the key step in the hydrogenation of iminium ion catalyzed by a P-P* ruthenium hydride complex, see: (a) Magee, M. P.; Norton, J. R. J. Am. Chem. Soc. 2001, 123, 1778. (b) Rossen, K. Angew. Chem., Int. Ed. 2001, 40, 4611.
65. Ruthenium enolates were also proposed as intermediates in the reports, see: (a) Alvarez, S. G.; Hasegawa, S.; Hirano, M.; Komiya, S. Tetrahedron Lett. 1998, 39, 5209. (b) Chang, S.; Na, Y.; Choi, E.; Kim, S. Org. Lett. 2001, 3, 2089. (c) Watanabe, M.; Ikagawa, A.; Wang, H.; Murata, K.; Ikariya, T. J. Am. Chem. Soc. 2004, 126, 11148 and references therein.
66. Ruthenium enolates were also proposed as intermediates in the reports, see: (a) Alvarez, S. G.; Hasegawa, S.; Hirano, M.; Komiya, S. Tetrahedron Lett. 1998, 39, 5209. (b) Chang, S.; Na, Y.; Choi, E.; Kim, S. Org. Lett. 2001, 3, 2089. (c) Watanabe, M.; Ikagawa, A.; Wang, H.; Murata, K.; Ikariya, T. J. Am. Chem. Soc. 2004, 126, 11148 and references therein.
67. Ruthenium enolates were also proposed as intermediates in the reports, see: (a) Alvarez, S. G.; Hasegawa, S.; Hirano, M.; Komiya, S. Tetrahedron Lett. 1998, 39, 5209. (b) Chang, S.; Na, Y.; Choi, E.; Kim, S. Org. Lett. 2001, 3, 2089. (c) Watanabe, M.; Ikagawa, A.; Wang, H.; Murata, K.; Ikariya, T. J. Am. Chem. Soc. 2004, 126, 11148 and references therein.
68. For the details of the synthesis of the chiral ligands and the physical and spectroscopic data of 2c,d,h, see the Supporting Information.
69. For the physical and spectroscopic data of the products, see the Supporting Information.