Highly enantioselective construction of the α-chiral center of amides via iridium-catalyzed hydrogenation of α,β-unsaturated amides

Advanced Synthesis and Catalysis

Volumn 351, Issue 9, 2009, Pages 1224-1228

  Lu, Wei Jing ^a   Hou, Xue Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Amides; Enantioselectivity; Hydrogenation; Iridium; P,N ligands

Indexed keywords

EID: 67549099240     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900080     Document Type: Article

References (96)

1. Some examples : a) Z. Lu, J. Bohn, T. Rano, C. A. Rutkowski, A. L. Simcoe, D. B. Olsen, W. A. Schleif, A. Carella, L. Gabryelski, L. Jin, J. H. Lin, E. Emini, K. Chapman, J. R. Tata, Bioorg. Med. Chem. Lett. 2005, 15, 5311;
2. b) D. Roche, J. Greiner, A. M. Aubertin, R Vierling, Bioconjugate Chem. 2006, 17, 1568;
3. c) A. K. Ghosh, N. Kumaragurubaran, L. Hong, S. S. Kulkarni, X. Xu, W. Chang, V. Weerasena, R. Turner, G. Koelsch, G. Bilcer, J. Tang, J. Med. Chem. 2007, 50, 2399;
4. d) J. D. Sadowsky, W. D. Fairlie, E. B. Hadley, H.-S. Lee, N. Umezawa, Z. Nikolovska-Coleska, S. Wang, D. C. S. Huang, Y. Tomita, S. H. Gellman, J. Am. Chem. Soc. 2007, 129, 139;
5. e) D. Lu, R. Vince, Bioorg. Med. Chem. Lett. 2007, 17, 5614;
6. f) T. Sauvaître, M. Barlier, D. Herlem, N. Gresh, A. Chiaroni, D. Guenard, C. Guillou, J. Med. Chem. 2007, 50, 5311;
7. g) J. Li, J. Dai, X. Chen, P. Zhu, J. Nat Prod. 2007, 70, 1846;
8. h) A. Fürstner, M. Bindl, Angew. Chem. 2007, 119, 9435;
9. Angew Chem. Int. Ed. 2007, 46, 9275;
10. i) G. Shen, J. Zhu, A. M. Simpson, D. Pei, Bioorg. Med. Chem. Lett. 2008, 18, 3060.
11. a) D. A. Evans, M. D. Ennis, D.J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737;
12. b) A. G. Myers, B. H. Yang, H. Chen, J. L. Gleason, J. Am. Chem. Soc. 1994, 116, 9361;
13. c) W. Oppolzer, C. Darcel, P. Rochet, S. Rosset, J. D. Brabander, Helv. Chim. Acta 1997, 80, 1319;
14. d) P. C. Hutchison, T.D. Heightman, D.J. Procter, Org. Lett. 2002, 4, 4583;
15. e) P. C. Hutchison, T. D. Heightman, D. J. Procter, J. Org. Chem. 2004, 69, 790;
16. f) A. M. McGhee, J.C. Kizirian, D.J. Procter, J. Org. Biomol. Chem. 2007, 5, 1021.
17. a) For a review, see: K. Rück, Angew. Chem. 1995, 107, 475;
18. Angew. Chem. Int. Ed. Engl. 1995, 34, 433;
19. some examples of chiral auxiliaries-induced synthesis of amides with an α-chiral center:
20. b) H.-s. Moon, N.E. Schore, M.J. Kurth, Tetrahedron Lett. 1994, 35, 8915;
21. c) K. Oertel, G. Zech, H. Kunz, Angew. Chem. 2000, 112, 1489;
22. Angew. Chem. Int. Ed. 2000, 39, 1431;
23. d) D. R. Dragoli, M. T. Burdett, J. A. Ellman, J. Am. Chem. Soc. 2001, 123, 10127; R-hydroxyvaline auxiliary:
24. e) S. N. Savinov, D.J. Austin, Org. Lett. 2002, 4, 1419;
25. f) G. Desimoni, G. Faita, A. Galbiati, D. Pasini, P. Quadrelli, F. Rancati, Tetrahedron: Asymmetry 2002, 13, 333;
26. g) A. Tessier, J. Pytkowicz, T. Brigaud, Angew. Chem. 2006, 118, 3759;
27. Angew. Chem. Int. Ed. 2006, 45, 3677;
28. h) D. A. Kummer, W. J. Chain, M. R. Morales, O. Quiroga, A. G. Myers, J. Am. Chem. Soc. 2008, 130, 13231.
29. a) B. M. Trost, M. U. Frederiksen, Angew. Chem. 2005, 117, 312;
30. Angew. Chem. Int. Ed. 2005, 44, 308;
31. b) B. M. Trost, Y. Zhang, J. Am. Chem. Soc. 2006, 128, 4590;
32. c) K. Zhang, Q. Peng, X. L. Hou, Y. D. Wu, Angew. Chem. 2008, 120, 1765;
33. Angew. Chem. Int. Ed. 2008, 47, 1741.
34. For some reviews, see : a) J. G. de Vries, C. J. Elsevier, (Eds.), The Handbook of Homogeneous Hydrogenation, Wiley-VCH, Weinheim, 2007;
35. b) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069;
36. c) R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 40;
37. Angew. Chem. Int. Ed. 2001, 40, 40;
38. d) H. U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103;
39. e) W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029;
40. f) T. Jerphagnon, J. L. Renaud, C. Bruneau, Tetrahedron: Asymmetry 2004, 15, 2101;
41. g) W. Zhang, Y. Chi, X. Zhang, Acc. Chem. Res. 2007, 40, 1278;
42. h) A. J. Minnaard, B. L. Feringa, L. Lefort, J. G. de Vries, Acc. Chem. Res. 2007, 40,1267;
43. i) W. P. Hems, M. Groarke, A. Zanotti-Gerosa, G. A. Grasa, Acc. Chem. Res. 2007, 40,1340;
44. J) F.D. Klingler, Acc. Chem. Res. 2007, 40, 1367;
45. k) Y. G. Zhou, Acc. Chem. Res. 2007, 40, 1357;
46. l) H.-U. Blaser, B, Pugin, F. Spindler, M. Thommen, Acc. Chem. Res. 2007, 40,1240;.
47. Some reviews oin Ir-catalyzed asymmetric hydrogenation, see : a) A. Pfaltz, J. Blankenstein, R. Hilgraf, E. Hörmann, S. Mclntyre, F. Menges, M. Schönleber, S. P. Smidt, B. Wüstenberg, N. Zimmermann, Adv. Synth. Catal. 2003, 345, 33;
48. b) X. Cui, K. Burgess, Chem. Rev. 2005, 105, 3272;
49. c) K. Källström, I. Munslow, P. G. Anderson, Chem. Eur. J. 2006, 12, 3194;
50. d) S. J. Roseblade, A. Pfaltz, Acc. Chem. Res. 2007, 40,1402.
51. Some examples of Ir-catalyzed asymmetric hydrogenation, see: a) H.-U. Blaser, F. Spindler, Top. Catal. 1997, 4, 275;
52. b) A. Lightfoot, P. Schnider, A. Pfaltz, Angew. Chem. 1998, 110, 3047;
53. Angew. Chem. Int. Ed. 1998, 37, 2897;
54. c) S. Kainz, A. Brinkmann, W. Leitner, A. Pfaltz, J. Am. Chem. Soc. 1999, 121, 6421;
55. d) D. Xiao, X. Zhang, Angew. Chem. 2001, 113, 3533;
56. Angew. Chem. Int. Ed. 2001, 40, 3425;
57. e) W. B. Wang, S. M. Lu, P. Y. Yang, X. W. Han, Y. G. Zhou, J. Am. Chem. Soc. 2003, 125, 10536;
58. f) Y. Fan, X. Cui, K. Burgess, M. B. Hall, J. Am. Chem. Soc. 2004, 126, 16688;
59. g) S. M. Lu, X. W. Han, Y. G. Zhou, Adv. Synth. Catal. 2004, 346, 909;
60. h) K. H. Lam, L. Xu, L. Feng, Q. H. Fan, F. L. Lam, W. Lo, A. S. C. Chan, Adv. Synth. Catal. 2005, 347, 1755;
61. i) C. Moessner, C. Bolm, Angew. Chem. 2005, 117, 7736
62. Angew. Chem. Int. Ed. 2005, 44, 7564;
63. j) L. Xu, K. H. Lam, J. Ji, J. Wu, Q. H. Fan, W. H. Lo, A. S. C. Chan, Chem. Commun. 2005, 1390;
64. k) M. T. Reetz, X. Li, Chem. Commun. 2006, 2159;
65. l) S. Bell, B. Wüstenberg, S. Kaiser, F. Menges, T. Netscher, A. Pfaltz, Science 2006, 311, 642;
66. m) S. F. Zhu, J. B. Xie, Y. Z. Zhang, S. Li, Q. L. Zhou, J. Am. Chem. Soc. 2006, 128, 12886;
67. n) C. Hedberg, K. Källström, P. Brandt, L. K. Hansen, P. G. Andersson, J. Am. Chem. Soc. 2006, 128, 2995;
68. o) S. M. Lu, Y.Q. Wang, X.W. Han, Y.G. Zhou, Angew. Chem. 2006, 118, 2318;
69. Angew. Chem. Int. Ed. 2006, 45, 2260;
70. p) G. H. Hou, J. H. Xie, L. X. Wang, Q. L. Zhou, J. Am. Chem. Soc. 2006, 128, 11774;
71. q) M. N. Cheemala, P. Knochel, Org. Lett. 2007, 9, 3089;
72. r) M. Engman, J. S. Diesen, A. Paptchikhine, P. G. Andersson, J. Am. Chem. Soc. 2007, 129, 4536;
73. s) Z. J. Wang, G. J. Deng, Y Li, Y. M. He, W. J. Tang, Q. H. Fan, Org. Lett. 2007, 9, 1243;
74. t) F. Giacomina, A. Meetsma, L. Panella, L. Lefort, A. H. M. de Vries, J. G. de Vries, Angew. Chem. 2007, 119, 1519;
75. Angew. Chem. Int. Ed. 2007, 46,1497;
76. u) M. G. Schrems, E. Neumann, A. Pfaltz, Angew. Chem. 2007, 119, 8422;
77. Angew. Chem. Int. Ed. 2007, 46, 8274;
78. v) J. Li, Q. Li, X. Wu, Y. Gao, D. Xu, L. Kong, Tetrahedron: Asymmetry 2007, 18, 629;
79. w) Y. Wang, T. Sturm, M. Steurer, V. B. Arion, K. Mereiter, F. Spindler, W. Weissensteiner, Organometallics 2008, 27, 1119.
80. a) S. Li, S. F. Zhu, C. M. Zhang, S. Song, Q. L. Zhou, J. Am. Chem. Soc. 2008, 130, 8584;
81. b) S. M. Lu, C. Bolm, Angew. Chem. 2008, 120, 9052;
82. Angew. Chem. Int. Ed. 2008, 47, 8920;
83. c) Y. Zhu, K. Burgess, J. Am. Chem. Soc. 2008, 130, 8894.
84. W. J. Lu, Y. W. Chen, X. L. Hou, Angew. Chem. 2008, 120, 10287;
85. Angew Chem. Int. Ed. 2008, 47,10133.
86. a) J. Zhou, J. W. Ogle, Y. Fan, V Banphavichit(Bee), Y. Zhu, K. Burgess, Chem. Eur. J. 2007, 13, 7162;
87. 4 has also been reported: Y. Ohtsuka, T. Ikeno, T. Yamada, Tetrahedron: Asymmetry 2003, 14, 967.
88. a) G. Helmchen, A. Pfaltz, Acc. Chem. Res. 2000, 33, 336;
89. b) S. J. Roseblade, A. Pfaltz, Acc. Chem. Res. 2007, 40, 1402.
90. a) X. L. Hou, D. X. Dong, K. Yuan Tetrahedron: Asymmetry 2004, 15, 2189;
91. b) W. Q. Wu, Q. Peng, D. X. Dong, X. L. Hou, Y. D. Wu, J. Am. Chem. Soc. 2008, 130, 9717.
92. a) T. Sammakia, H. A. Latham, J. Org. Chem. 1995, 60, 6002;
93. b) Y. Nishibayashi, S. Uemura, Synlett 1995, 79;
94. c) C.J. Richards, T. Damalidis, D.E. Hibbs, M. B. Hursthouse, Synlett 1995, 74.
95. a) R. H. Baker, L. E. Linn J. Am. Chem. Soc. 1948, 70, 3721;
96. [3g]