Enantioselective conjugate addition of dialkylzinc to cyclic enones catalyzed by chiral binaphthyldiamine-copper(I) complexes

Tetrahedron Letters

Volumn 48, Issue 49, 2007, Pages 8590-8594

  Hatano, Manabu ^a   Asai, Takafumi ^a   Ishihara, Kazuaki ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; ALKYL GROUP; COPPER COMPLEX; DIALKYLZINC; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONJUGATION; CYCLIZATION; ENANTIOSELECTIVITY; PKA;

EID: 35748962623     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.061     Document Type: Article

References (73)

1. Jacobsen E.N., Pfaltz A., and Yamamoto H. Comprehensive Asymmetric Catalysis (1999), Springer, New York
2. For reviews:. Rossiter B.E., and Swingle N.M. Chem. Rev. 92 (1992) 771
3. Krause N., and Gerold A. Angew. Chem., Int. Ed. 36 (1997) 186
4. Sibi M.P., and Manyem S. Tetrahedron 56 (2000) 8033
5. Krause N., and Hoffmann-Röder A. Synthesis (2001) 171
6. Alexakis A., and Benhaim C. Eur. J. Org. Chem. (2002) 3221
7. Pioneering works with P-ligands and P,O-ligands:. Feringa B.L., Pineschi M., Arnold L.A., Imbos R., and de Vries A.H.M. Angew. Chem., Int. Ed. 36 (1997) 2620
8. Alexakis A., Vastra J., Burton J., Benhaim C., and Mangeney P. Tetrahedron Lett. 39 (1998) 7869
9. Yan M., Yang L.-W., Wong K.-Y., and Chan A.S.C. Chem. Commun. (1999) 11
10. Yan M., Zhou Z.-Y., and Chan A.S.C. Chem. Commun. (2000) 115
11. Alexakis A., Benhaim C., Rosset S., and Humam M. J. Am. Chem. Soc. 124 (2002) 5262
12. Taira S., Crépy K.V.L., and Imamoto T. Chirality 14 (2002) 386
13. Huttenloch O., Laxman E., and Waldmann H. Chem. Commun. (2002) 673
14. Choi Y.H., Choi J.H., Yang H.Y., and Kim Y.H. Tetrahedron: Asymmetry 13 (2002) 801
15. Reetz M.T., Gosberg A., and Moulin D. Tetrahedron Lett. 43 (2002) 1189
16. Watanabe T., Knöpfel T.F., and Carreira E.M. Org. Lett. 5 (2003) 4557
17. Liang L., Su L., Li X., and Chan A.S.C. Tetrahedron Lett. 44 (2003) 7217
18. Monti C., Gennari C., Steele R.M., and Piarulli U. Eur. J. Org. Chem. (2004) 3557
19. Ito K., Eno S., Saito B., and Katsuki T. Tetrahedron Lett. 46 (2005) 3981
20. Takahashi Y., Yamamoto Y., Katagiri K., Danjo H., Yamaguchi K., and Imamoto T. J. Org. Chem. 70 (2005) 9009
21. Palais L., Mikhel I.S., Bournaund C., Micouin L., Falciola C.A., Vuagnoux-d'Augustin M., Rosset S., Bernardinelli G., and Alexakis A. Angew. Chem., Int. Ed. 46 (2007) 7606
22. Pioneering works with N,N-ligands, P,N-ligands, and P,O,N-ligands. Hu X., Chen H., and Zhang X. Angew. Chem., Int. Ed. 38 (1999) 3518
23. Chataigner I., Gennari C., Piarulli U., and Caccarelli S. Angew. Chem., Int. Ed. 39 (2000) 916
24. Escher I.H., and Pfaltz A. Tetrahedron 56 (2000) 2879
25. Morimoto T., Yamaguchi Y., Suzuki M., and Saitoh A. Tetrahedron Lett. 41 (2000) 10025
26. Degrado S.J., Mizutani H., and Hoveyda A.H. J. Am. Chem. Soc. 123 (2001) 755
27. Schinnerl M., Seitz M., Kaiser A., and Reiser O. Org. Lett. 3 (2001) 4259
28. Mizutani H., Degrado S.J., and Hoveyda A.H. J. Am. Chem. Soc. 124 (2002) 779
29. Shintani R., and Fu G.C. Org. Lett. 4 (2002) 3699
30. Krauss I.J., and Leighton J.L. Org. Lett. 5 (2003) 3201
31. Hu Y., Liang X., Wang J., Zheng Z., and Hu X. J. Org. Chem. 68 (2003) 4542
32. Wan H., Hu Y., Liang Y., Gao S., Wang J., Zheng Z., and Hu X. J. Org. Chem. 68 (2003) 8277
33. Liang Y., Gao S., Wan H., Hu Y., Chen H., Zheng Z., and Hu X. Tetrahedron: Asymmetry 14 (2003) 3211
34. Hu Y., Liang X., Wang J., Zheng Z., and Hu X. Tetrahedron: Asymmetry 14 (2003) 3907
35. Hird A.W., and Hoveyda A.H. Angew. Chem., Int. Ed. 42 (2003) 1276
36. Morimoto T., Mochizuki N., and Suzuki M. Tetrahedron Lett. 45 (2004) 5717
37. Shi M., Wang C.-J., and Zhang W. Chem. Eur. J. 10 (2004) 5507
38. Shi M., and Zhang W. Adv. Synth. Catal. 347 (2005) 535
39. Morimoto T., Obara N., Yoshida I., Tanaka K., and Kan T. Tetrahedron Lett. 48 (2007) 3093
40. Pioneering works with N-heterocyclic carbene ligands. Lee K.-S., Brown M.K., Hird A.W., and Hoveyda A.H. J. Am. Chem. Soc. 128 (2006) 7182
41. Bordwell F.G., Algrim D., and Vanier N.R. J. Org. Chem. 42 (1977) 1817
42. Bordwell F.G., and Algrim D.J. J. Am. Chem. Soc. 110 (1988) 2946
43. Multi-functionalized polymetallic catalyses. Oshima K. J. Organomet. Chem. 575 (1999) 1
44. Boudier A., Bromm L.O., Lotz M., and Knochel P. Angew. Chem., Int. Ed. 39 (2000) 4414
45. Trost B.M., and Ito H. J. Am. Chem. Soc. 122 (2000) 12003
46. Trost B.M., Ito H., and Silcoff E.R. J. Am. Chem. Soc. 125 (2001) 3367
47. Matsunaga S., Oshima T., and Shibasaki M. Adv. Synth. Catal. 344 (2002) 3
48. Trost B.M., and Yeh V.S.C. Angew. Chem., Int. Ed. 41 (2002) 861
49. Shibasaki M., Kanai M., and Funabashi K. Chem. Commun. (2002) 1989
50. Knochel P., Dohle W., Gommermann N., Kneisel F.F., Kopp F., Korn T., Sapountzis I., and Vu V.A. Angew. Chem., Int. Ed. 42 (2003) 4302
51. Shinokubo H., and Oshima K. Eur. J. Org. Chem. (2004) 2081
52. Yorimitsu H., and Oshima K. Angew. Chem., Int. Ed. 44 (2005) 4435
53. Kanai M., Kato N., Ichikawa E., and Shibasaki M. Pure Appl. Chem. 77 (2005) 2047
54. Kanai M., Kato N., Ichikawa E., and Shibasaki M. Synlett (2005) 1491
55. Trost B.M., Weiss A.H., and Jacobi von Wangelin A. J. Am. Chem. Soc. 128 (2006) 8
56. Shibasaki M., and Matsunaga S. Chem. Rev. Soc. 35 (2006) 269
57. Shibasaki M., and Kanai M. Org. Biomol. Chem. 5 (2007) 2027
58. In the course of our study, functionalized polymetallic catalyses for carbonyl compounds have been reported. Hatano M., Matsumura T., and Ishihara K. Org. Lett. 7 (2005) 573
59. Hatano M., Miyamoto T., and Ishihara K. Adv. Synth. Catal. 347 (2005) 1561
60. Hatano M., Asai T., and Ishihara K. Chem. Lett. 35 (2006) 172
61. Hatano M., Miyamoto T., and Ishihara K. Synlett (2006) 1762
62. Hatano M., Miyamoto T., and Ishihara K. J. Org. Chem. 71 (2006) 6474
63. Hatano M., Suzuki S., and Ishihara K. J. Am. Chem. Soc. 128 (2006) 9998
64. Hatano M., Takagi E., Arinobe M., and Ishihara K. J. Orgamomet. Chem. 692 (2007) 569
65. Hatano M., Miyamoto T., and Ishihara K. Org. Lett. 9 (2007) 4535
66. The combined use of 1 and 6 or 2 and 6 was not effective, and 2 was obtained in poor yield and low enantioselectivities (<10% ee).
67. 2Zn with 5 mol % of CuCl and 10 mol % of 6 did not proceed at 0 °C for 5 h.
68. 2O), to give the desired products (2) in 95% yield (119.9 mg). The enantiomeric purity was determined by GC on chiral column (γ-TA) (76% ee, S).
69. 2Zn (1.0 M solution in heptane) were used in the reaction without further solvents. Similar procedures using two different organozinc reagents in the enantioselective phenylation of aldehydes have been reported. Bolm C., Hermanns N., Hildebrand J.P., and Muñiz K. Angew. Chem., Int. Ed. 39 (2000) 3465
70. Also see reviews:. Schmidt F., Stemmler R.T., Rudolph J., and Bolm C. Chem. Soc. Rev. 35 (2006) 454
71. Hatano M., Miyamoto T., and Ishihara K. Curr. Org. Chem. 11 (2007) 127
72. Enantioselective conjugate addition of dialkylzinc to acyclic enones, such as chalcone and diethyl 2-ethylidenemalonate, catalyzed by Cu(II)/5/6 system gave the corresponding products in low yields with low enantioselectivities (<20% ee).
73. 2 did not occur.