Rh-catalyzed direct enantioselective alkynylation of α-ketiminoesters

Chemistry - A European Journal

Volumn 19, Issue 26, 2013, Pages 8417-8420

  Morisaki, Kazuhiro ^a   Sawa, Masanao ^a   Nomaguchi, Jun Ya ^a   Morimoto, Hiroyuki ^a   Takeuchi, Yosuke ^b   Mashima, Kazushi ^b   Ohshima, Takashi ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

ketiminoester; alkynylation; amino acids; asymmetric catalysis; tetrasubstituted carbon atom

Indexed keywords

ALKYNYLATIONS; AMINO ACID DERIVATIVES; ASYMMETRIC CATALYSIS; CARBON ATOMS; ENANTIOSELECTIVE; HIGH YIELD; ROOM TEMPERATURE;

AMINO ACIDS; ENANTIOSELECTIVITY; RHODIUM;

CATALYSIS;

AMINO ACID; COORDINATION COMPOUND; DRUG DERIVATIVE; ESTER; PARGYLINE; PROPARGYLAMINE; PROPYLAMINE; PROTON; RHODIUM;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; TEMPERATURE;

AMINO ACIDS; CATALYSIS; COORDINATION COMPLEXES; ESTERS; PARGYLINE; PROPYLAMINES; PROTONS; RHODIUM; STEREOISOMERISM; TEMPERATURE;

EID: 84879164787     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301237     Document Type: Article

References (62)

1. For examples, see: a) M. Konishi, H. Ohkuma, T. Tsuno, T. Oki, G. D. VanDuyne, J. Clardy, J. Am. Chem. Soc. 1990, 112, 3715;
2. b) T. Yoon, M. D. Shair, S. J. Danishefsky, G. K. Shulte, J. Org. Chem. 1994, 59, 3752;
3. c) M. A. Huffman, N. Yasuda, A. E. DeCamp, E. J. J. Grabowski, J. Org. Chem. 1995, 60, 1590;
4. d) G. S. Kauffman, G. D. Harris, R. L. Dorow, B. R. P. Stone, R. L. Parsons, Jr., J. A. Pesti, N. A. Magnus, J. M. Fortunak, P. N. Confalone, W. A. Nugent, Org. Lett. 2000, 2, 3119;
5. e) B. Jiang, M. Xu, Angew. Chem. 2004, 116, 2597;
6. Angew. Chem. Int. Ed. 2004, 43, 2543;
7. f) B. M. Trost, C. K. Chung, A. B. Pinkerton, Angew. Chem. 2004, 116, 4427;
8. Angew. Chem. Int. Ed. 2004, 43, 4327;
9. g) J. J. Fleming, J. Du Bois, J. Am. Chem. Soc. 2006, 128, 3926.
10. For reviews, see: a) P. G. Cozzi, R. Hilgraf, N. Zimmermann, Eur. J. Org. Chem. 2004, 4095;
11. b) B. M. Trost, A. H. Weiss, Adv. Synth. Catal. 2009, 351, 963;
12. c) P. de Armas, D. Tejedor, F. García-Tellado, Angew. Chem. 2010, 122, 1029;
13. Angew. Chem. Int. Ed. 2010, 49, 1013;
14. d) W.-J. Yoo, L. Zhao, C.-J. Li, Aldrichimica Acta 2011, 44, 43;
15. e) V. A. Peshkov, O. P. Pereshivko, E. V. Van der Eycken, Chem. Soc. Rev. 2012, 41, 3790.
16. a) B. M. Trost, Science 1991, 254, 1471;
17. b) D. E. Frantz, R. Fssler, C. S. Tomooka, E. M. Carreira, Acc. Chem. Res. 2000, 33, 373.
18. For selected examples, see: a) C. Wei, C.-J. Li, J. Am. Chem. Soc. 2002, 124, 5638;
19. b) C. Koradin, K. Polborn, P. Knochel, Angew. Chem. 2002, 114, 2651;
20. Angew. Chem. Int. Ed. 2002, 41, 2535;
21. c) T. F. Knçpfel, P. Aschwanden, T. Ichikawa, T. Watanabe, E. M. Carreira, Angew. Chem. 2004, 116, 6097;
22. Angew. Chem. Int. Ed. 2004, 43, 5971;
23. d) A. Bisai, V. K. Singh, Org. Lett. 2006, 8, 2405;
24. e) M. Rueping, A. P. Antonchick, C. Brinkmann, Angew. Chem. 2007, 119, 7027;
25. Angew. Chem. Int. Ed. 2007, 46, 6903;
26. f) Y. Lu, T. C. Johnstone, B. A. Arndtsen, J. Am. Chem. Soc. 2009, 131, 11284;
27. g) S. Nakamura, M. Ohara, Y. Nakamura, N. Shibata, T. Toru, Chem. Eur. J. 2010, 16, 2360;
28. see also Ref. [2].
29. a) C. Fischer, E. M. Carreira, Synthesis 2004, 1497;
30. b) M. J. Aliaga, D. J. Ramn, M. Yus, Org. Biomol. Chem. 2010, 8, 43;
31. c) O. P. Pereshivko, V. A. Peshkov, E. V. Van der Eycken, Org. Lett. 2010, 12, 2638;
32. d) M. Cheng, Q. Zhang, X.-Y. Hu, B.-G. Li, J.-X. Ji, A. S. C. Chan, Adv. Synth. Catal. 2011, 353, 1274;
33. e) C. E. Meyet, C. J. Pierce, C. H. Larsen, Org. Lett. 2012, 14, 964;
34. f) C. J. Pierce, C. H. Larsen, Green Chem. 2012, 14, 2672;
35. g) C. J. Pierce, M. Nguyen, C. H. Larsen, Angew. Chem. 2012, 124, 12455;
36. Angew. Chem. Int. Ed. 2012, 51, 12289.
37. T. Hashimoto, M. Omote, K. Maruoka, Angew. Chem. 2011, 123, 9114;
38. Angew. Chem. Int. Ed. 2011, 50, 8952.
39. L. Yin, Y. Otsuka, H. Takada, S. Mouri, R. Yazaki, N. Kumagai, M. Shibasaki, Org. Lett. 2013, 15, 698.
40. C. Toniolo, F. Formaggio, B. Kaptein, Q. B. Broxterman, Synlett 2006, 1295.
41. Reviews: a) J. L. AceÇa, A. E. Sorochinsky, V. A. Soloshonok, Synthesis 2012, 1591;
42. b) R. Smits, C. D. Cadicamo, K. Burger, B. Koksch, Chem. Soc. Rev. 2008, 37, 1727.
43. For selected examples, see: a) D. Enders, K. Gottfried, G. Raabe, Adv. Synth. Catal. 2010, 352, 3147;
44. b) Y.-L. Liu, T.-D. Shi, F. Zhou, X.-L. Zhao, X. Wang, J. Zhou, Org. Lett. 2011, 13, 3826;
45. c) S. Y. Kim, S. J. Kim, D. O. Jang, Chem. Eur. J. 2010, 16, 13046;
46. d) R. Husmann, E. Sugiono, S. Mersmann, G. Raabe, M. Rueping, C. Bolm, Org. Lett. 2011, 13, 1044;
47. e) G. Huang, J. Yang, X. Zhang, Chem. Commun. 2011, 47, 5587;
48. f) F.-G. Zhang, H. Ma, Y. Zheng, J.-A. Ma, Tetrahedron 2012, 68, 7663;
49. see also Ref. [9].
50. For reviews, see: a) H. Nishiyama, Chem. Soc. Rev. 2007, 36, 1133;
51. b) H. Nishiyama, J.-i. Ito, Chem. Rec. 2007, 7, 159;
52. c) T. Shiomi, T. Adachi, K. Toribatake, L. Zhou, H. Nishiyama, Chem. Commun, 2009, 5987;
53. d) H. Nishiyama, J.-i. Ito, Chem. Commun. 46, 2010, 203.
54. Preliminary results were presented at the 13th Belgian Organic Synthesis Symposium (BOSS XIII): T. Ohshima, K. Morisaki, J. Nomaguchi, H. Morimoto, T. Kawabata, Y. Takeuchi, K. Mashima, Book of Abstracts, BOSS XIII, P089.
55. T. Ohshima, T. Kawabata, Y. Takeuchi, T. Kakinuma, T. Iwasaki, T. Yonezawa, H. Murakami, H. Nishiyama, K. Mashima, Angew. Chem. 2011, 123, 6420;
56. Angew. Chem. Int. Ed. 2011, 50, 6296.
57. For catalytic enantioselective alkynylation of a-ketiminoesters with stoichiometric amounts of organometallic reagents, see Ref. [10e] and [10f].
58. K. Burger, E. Hçß, K. Gaa, N. Sewald, C. Schierlinger, Z. Naturforsch. 1991, 46b, 361.
59. G. Blay, A. Brines, A. Monlen, J. R. Pedro, Chem. Eur. J. 2012, 18, 2440.
60. T. Iwasaki, K. Agura, Y. Maegawa, Y. Hayashi, T. Ohshima, K. Mashima, Chem. Eur. J. 2010, 16, 11567;
61. a) S. N. Osipov, P. Tsouker, L. Hennig, K. Burger, Tetrahedron 2004, 60, 271;
62. b) S. N. Osipov, A. S. Golubev, N. Sewald, K. Burger, Tetrahedron Lett. 1997, 38, 5965.