Asymmetric hydrogenation of aromatic heterocyclic ketones catalyzed by the MsDPEN-Cp*Ir(III) complex

Heterocycles

Volumn 80, Issue 1, 2010, Pages 141-147

  Utsumi, Noriyuki ^b   Tsutsumi, Kunihiko ^b   Watanabe, Masahiko ^b   Murata, Kunihiko ^b   Arai, Noriyoshi ^a   Kurono, Nobuhito ^a   Ohkuma, Takeshi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b KANTO CHEMICAL CO INC   (Japan)

Author keywords

Asymmetric Hydrogenation; Chiral Alchohol; Enantioselective Reaction; Iridium Catalyst; Ketone

Indexed keywords

EID: 76949104423     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-09-S(S)34     Document Type: Article

References (33)

1. Reviews on asymmetric hydrogenation of ketones. Ohkuma T., and Noyori R. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 1 (1999), Springer, Berlin-Heidelberg 199-246
2. Ohkuma T., Kitamura M., and Noyori R. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis. 2nd ed. (2000), Wiley-VCH, New York 1-110
3. Ohkuma T., and Noyori R. In: Beller M., and Bolm C. (Eds). Transition Metals for Organic Synthesis. 2nd ed. Vol. 2 (2004), Wiley-VCH, Weinheim 29-113
4. Ohkuma T., and Noyori R. In: de Vries J.G., and Elsevier C.J. (Eds). The Handbook of Homogeneous Hydrogenation Vol. 3 (2007), Wiley-VCH, Weinheim 1105-1163
5. See for example:. Doucet H., Ohkuma T., Murata K., Yokozawa T., Kozawa M., Katayama E., England A.F., Ikariya T., and Noyori R. Angew. Chem. Int. Ed. 37 (1998) 1703
6. Ohkuma T., Koizumi M., Doucet H., Pham T., Kozawa M., Murata K., Katayama E., Yokozawa T., Ikariya T., and Noyori R. J. Am. Chem. Soc. 120 (1998) 13529
7. Ohkuma T., Koizumi M., Muñiz K., Hilt G., Kabuto C., and Noyori R. J. Am. Chem. Soc. 124 (2002) 6508
8. Arai N., Ooka H., Azuma K., Yabuuchi T., Kurono N., Inoue T., and Ohkuma T. Org. Lett. 9 (2007) 939
9. Arai N., Azuma K., Nii N., and Ohkuma T. Angew. Chem. Int. Ed. 47 (2008) 7457
10. Ooka H., Arai N., Azuma K., Kurono N., and Ohkuma T. J. Org. Chem. 73 (2008) 9084
11. Reviews:. Ohkuma T. J. Synth. Org. Chem. Jpn. 65 (2007) 1070
12. Noyori R., and Ohkuma T. Angew. Chem. Int. Ed. 40 (2001) 40
13. Ohkuma T., Sandoval C.A., Srinivasan R., Lin Q., Wei Y., Muñiz K., and Noyori R. J. Am. Chem. Soc. 127 (2005) 8288
14. Arai N., Suzuki K., Sugizaki S., Sorimachi H., and Ohkuma T. Angew. Chem. Int. Ed. 47 (2008) 1770
15. Tsutsumi K., Katayama T., Utsumi N., Murata K., Arai N., Kurono N., and Ohkuma T. Org. Proc. Res. Dev. 13 (2009) 625
16. Ohkuma T., Utsumi N., Tsutsumi K., Murata K., Sandoval C.A., and Noyori R. J. Am. Chem. Soc. 128 (2006) 8724
17. Sandoval C.A., Ohkuma T., Utsumi N., Tsutsumi K., Murata K., and Noyori R. Chem. Asian J. 1-2 (2006) 102
18. 6-arene/TsDPEN-Ru(II) complexes see:. Ohkuma T., Tsutsumi K., Utsumi N., Arai N., Noyori R., and Murata K. Org. Lett. 9 (2007) 255
19. Ohkuma T., Utsumi N., Watanabe M., Tsutsumi K., Arai N., and Murata K. Org. Lett. 9 (2007) 2565
20. 13C NMR (100 MHz, CDCI3) δ 72.2, 79.1, 110.6, 121.0, 125.4, 128.2, 130.8, 160.2.
21. 1H-NMR analysis after conversion to the (R)- and (S)-MTPA esters as described in the literature, See:. Ohtani I., Kusumi T., Kashman Y., and Kakisawa H. J. Am. Chem. Soc. 113 (1991) 4092
22. 3) δ 29.8, 36.0, 76.5, 124.2, 124.9, 126.7, 128.3, 143.3, 145.0.
23. For asymmetric hydrogenation of cycloalkanones catalyzed by the BINAP-Ir(I)-aminophosphine system, see:. Zhang X., Taketomi T., Yoshizumi T., Kumobayashi H., Akutagawa S., Mashima K., and Takaya H. J. Am. Chem. Soc. 115 (1993) 3318
24. For asymmetric hydrogenation of aromatic ketones catalyzed by Ru(II) complexes with some amine-based chiral ligands, see:. Huang H., Okuno T., Tsuda K., Yoshimura M., and Kitamura M. J. Am. Chem. Soc. 128 (2006) 8716
25. Ito M., Endo Y., and Ikariya T. Organometallics 27 (2008) 6053
26. 3) δ 30.8, 61.9, 63.2, 117.1, 120.6, 124.3, 129.6, 129.7, 154.6.
27. 3) δ 20.5, 31.0, 61.9, 63.3, 116.8, 123.9, 129.79, 129.83, 130.4, 152.3.
28. 3) δ 30.6,62.2, 63.1, 118.5, 125.2, 125.6, 129.1, 129.6, 153.2.
29. 3) δ 21.5, 30.0, 66.5, 124.3, 126.7, 128.4, 130.3, 133.2, 134.6.
30. 9
31. 9
32. For asymmetric hydrogenation of 1-tetralones catalyzed by BINAP/chiral 1,4-diamine-Ru(II) complexes, see:. Ohkuma T., Hattori T., Ooka H., Inoue T., and Noyori R. Org. Lett. 6 (2004) 2681
33. 3) δ 18.7, 29.2, 32.2, 68.1, 126.1, 127.5, 128.6, 129.0, 137.1, 138.7.