Iridium complex bearing a chiral hydroxy-amide functionalized N-heterocyclic carbene: A catalyst precursor for asymmetric transfer hydrogenation

Tetrahedron Letters

Volumn 52, Issue 50, 2011, Pages 6788-6791

  Chiyojima, Hiroyuki ^a   Sakaguchi, Satoshi ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

Asymmetric transfer hydrogenation; Catalyst precursor; Highly tunable NHC ligand; Iridium complex; N Heterocyclic carbene

Indexed keywords

ACETOPHENONE; AMIDE; HETEROCYCLIC COMPOUND; IRIDIUM;

ARTICLE; CATALYST; CHIRALITY; CRYSTALLOGRAPHY; ENANTIOSELECTIVITY; HYDROGENATION;

EID: 80755135409     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.057     Document Type: Article

References (45)

1. For selected recent reviews: O. Kühl Funtionalised N-Heterocyclic Carbene Complexes 2010 Wiley-VCH Weinheim, Germany
2. F. Glorius N-Heterocyclic Carbenes in Transition Metal Catalysis 2007 Springer Berlin
3. S.P. Nolan N-Heterocyclic Carbenes in Synthesis 2006 Wiley-VCH Weinheim, Germany
4. H. Clavier, and S.P. Nolan Chem. Commun. 2010 841 861
5. S. Díez-González, N. Marion, and S.P. Nolan Chem. Rev. 109 2009 3612 3676
6. R. Corberán, E. Mas-Marzá, and E. Peris Eur. J. Inorg. Chem. 2009 1700 1716
7. D.R. Snead, H. Seo, and S. Hong Curr. Org. Chem. 12 2008 1370 1387
8. F.E. Hahn, and M.C. Jahnke Angew. Chem., Int. Ed. 47 2008 3122 3172
9. S. Würtz, and F. Glorius Acc. Chem. Res. 41 2008 1523 1533
10. M. Marion, and S.P. Nolan Acc. Chem. Res. 41 2008 1440 1449
11. E.A.B. Kantchev, C.J. O'Brien, and M.G. Organ Angew. Chem., Int. Ed. 46 2007 2768 2813
12. R.E. Douthwaite Coord. Chem. Rev. 251 2007 702 717
13. D. Pugh, and A.A. Danopoulos Coord. Chem. Rev. 251 2007 610 641
14. S.T. Liddle, I.S. Edworthy, and P.L. Arnold Chem. Soc. Rev. 36 2007 1732 1744
15. O. Kühl Chem. Soc. Rev. 36 2007 592 607
16. P.L. Arnold, and S.T. Liddle Chem. Commun. 2006 3959 3971
17. W. Kirmse Angew. Chem., Int. Ed. 43 2004 1767 1769
18. E. Peris, and R.H. Crabtree Coord. Chem. Rev. 248 2004 2239 2246
19. W.A. Herrmann Angew. Chem., Int. Ed. 41 2002 1290 1309
20. D. Bourissou, O. Guerret, F.P. Gabbaï, and G. Bertrand Chem. Rev. 100 2000 39 91
21. A.T. Normand, and K.J. Cavell Eur. J. Inorg. Chem. 2008 2781 2800
22. V. César, S. Bellemin-Laponnaz, and L.H. Gade Chem. Soc. Rev. 33 2004 619 636
23. M.C. Perry, and K. Burgess Tetrahedron: Asymmetry 14 2003 951 961
24. R. Malacea, R. Poli, and E. Manoury Coord. Chem. Rev. 254 2010 729 752
25. T. Ikariya, and A.J. Blacker Acc. Chem. Res. 40 2007 1300 1308 and references cited therein
26. H. Seo, B.Y. Kim, J.H. Lee, H.J. Park, H.U. Son, and Y.K. Chung Organometallics 22 2003 4783 4791
27. 2 combined with a chiral phosphine/NHC compound gave 34% ee: R. Hodgson, and R.E. Douthwaite J. Organomet. Chem. 690 2005 5822 5831
28. 24% ee was obtained with a bisisoquinoline-based chiral NHC-Ir(I) complex: W.A. Herrmann, D. Baskakov, E. Herdtweck, S.D. Hoffmann, T. Bunlaksananusorn, F. Rampf, and L. Rodefeld Organometallics 25 2006 2449 2456
29. Ir complex with a chiral hybrid imine/NHC ligand gave 43% ee: G. Dyson, J.-C. Frison, A.C. Whitwood, and R.E. Douthwaite Dalton Trans. 2009 7141 7151
30. During the course of our study, 60% ee was recorded by using a chelated ferrocene-based planar chiral NHC-Rh(I) complex: R. Jiang, X. Sun, W. He, H. Chen, and Y. Kuang Appl. Organometal. Chem. 23 2009 179 182
31. A chiral bis(NHC)-Ir(I) complex led to 14% ee, while 68% ee was achieved in the reduction of 2′,4′,6′-trimethylacetophenone: C. Diez, and U. Nagel Appl. Organometal. Chem. 24 2010 509 516
32. S. Sakaguchi, K.S. Yoo, J. O'Neill, J.H. Lee, T. Stewart, and K.W. Jung Angew. Chem., Int. Ed. 47 2008 9326 9329
33. S. Sakaguchi, M. Kawakami, J. O'Neill, K.S. Yoo, and K.W. Jung J. Organomet. Chem. 695 2010 195 200
34. K.S. Yoo, J. O'Neill, S. Sakaguchi, R. Giles, J.H. Lee, and K.W. Jung J. Org. Chem. 75 2010 95 101
35. R. Kamisue, and S. Sakaguchi J. Organomet. Chem. 696 2011 1910 1915
36. M. Okamoto, Y. Yamamoto, and S. Sakaguchi Chem. Commun. 2009 7363 7365
37. N. Shibata, M. Okamoto, Y. Yamamoto, and S. Sakaguchi J. Org. Chem. 75 2010 5707 5715
38. A. Harano, and S. Sakaguchi J. Organomet. Chem. 696 2011 61 67
39. M. Yoshimura, N. Shibata, M. Kawakami, and S. Sakaguchi Tetrahedron 2011 10.1016/j.tet.2011.04.028
40. D. Gnanamgari, E.L.O. Sauer, N.D. Schley, C. Butler, C.D. Incarvito, and R.H. Crabtree Organometallics 28 2009 321 325
41. Y. Tanabe, F. Hanasaka, K. Fujita, and R. Yamaguchi Organometallics 26 2007 4618 4626
42. R. Corberan, M. Sanau, and E. Peris J. Am. Chem. Soc. 128 2006 3974 3979
43. F. Hanasaka, K. Fujita, and R. Yamaguchi Organometallics 24 2005 3422 3433
44. F. Hanasaka, K.I. Fujita, and R. Yamaguchi Organometallics 23 2004 1490 1492
45. K.-s. Lee, K. Brown, A.W. Hird, and A.H. Hoveyda J. Am. Chem. Soc. 128 2006 7182 7184