Enantioselective allylation of ketones catalyzed by N,N′-dioxide and indium(III) complex

Journal of Organic Chemistry

Volumn 72, Issue 14, 2007, Pages 5227-5233

  Zhang, Xin ^a   Chen, Donghui ^a   Liu, Xiaohua ^a   Feng, Xiaoming ^a,b  

^a SICHUAN UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC INDUCTIVITY; BIFUNCTIONAL CATALYST; HOMOALLYLIC ALCOHOLS;

AMINO ACIDS; AROMATIC COMPOUNDS; CATALYSIS; ENANTIOSELECTIVITY; METAL COMPLEXES;

KETONES;

ALCOHOL; AMINO ACID; INDIUM; KETONE DERIVATIVE; METAL ION; OXIDE; PIPECOLIC ACID; PROLINE;

ALLYLATION; ARTICLE; CATALYST; ENANTIOSELECTIVITY; REACTION ANALYSIS; SYNTHESIS;

CATALYSIS; INDIUM; KETONES; LIGANDS; MOLECULAR STRUCTURE; OXIDES; STEREOISOMERISM; TEMPERATURE;

EID: 34447297533     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0706325     Document Type: Article

References (75)

1. For reviews, see: (a) Marshall, J. A. Chem. Rev. 1996, 96, 31-48.
2. (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293.
3. For representative examples, see: (c) Felpin, F. X.; Lebreton, J. J. Org. Chem. 2002, 67, 9192-9199.
4. (d) Nicolaou, K. C.; Kim, D. W.; Baati, R. Angew. Chem. 2002, 114, 3853-3856;
5. Angew. Chem., Int. Ed. 2002, 41, 3701-3704.
6. (e) Hoveyda, A. H.; Morken, J. P. Angew. Chem. 1996, 108, 1378-1401;
7. Angew. Chem., Int. Ed. 1996, 35, 1262-1284.
8. (f) Leighton, J. L.; Hornberger, K. R.; Hamblett, C. L. J. Am. Chem. Soc. 2000, 122, 12894-12895.
9. For reviews, see: Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763-2794.
10. For representative examples, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163.
11. (b) Denmark, S. E; Fu, J. J. Am. Chem. Soc. 2000, 122, 12021-12022.
12. (c) Denmark, S. E.; Fu, J.; Coe, D. M.; Su, X.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 2006, 71, 1513-1522.
13. (d) Denmark, S. E.; Fu, J.; Lawler, M. J. J. Org. Chem. 2006, 71, 1523-1536.
14. (e) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419-6420.
15. (f) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kočovský, P. Org. Lett. 2002, 4, 1047-1049.
16. (g) Malkov, A. V.; Bell, M.; Castelluzzo, F.; Kočovský, P. Org. Lett. 2005, 7, 3219-3222.
17. (h) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799-2801.
18. (i) Kina, A.; Shimada, T.; Hayashi, T. Adv. Synth. Catal. 2004, 346, 1169-1174.
19. (j) Pignataro, L.; Benaglia, M.; Annunziata, R.; Cinquini, M.; Cozzi, F. J. Org. Chem. 2006, 71, 1458-1463.
20. (k) Traverse, J. F.; Zhao, Y.; Hoveyda, A. H.; Snapper, M. L. Org. Lett. 2005, 7, 3151 -3154.
21. (l) Rabbat, P. M. A.; Valdez, S. C.; Leighton, J. L. Org. Lett. 2006, 8, 6119-6121.
22. (m) Teo, Y. C.; Tan, K. T.; Loh, T. P. Chem. Commun. 2005, 1318-1320.
23. Walsh, P. J.; Kim, J. G.; Camp, E. H. Org. Lett. 2006, 8, 4413-4416.
24. For representative examples of enantioselective allylation of ketones, see: (a) Leighton, J. L.; Burns, N. Z.; Hackman, B. M.; Ng, P. Y.; Powelson, I. A. Angew. Chem. 2006, 118, 3895-3897;
25. Angew. Chem., Int. Ed. 2006, 45, 3811-3813.
26. (b) Schaus, S. E.; Lou, S.; Moquist, P. N. J. Am. Chem. Soc. 2006, 128, 12660-12661.
27. (c) Soderquist, J. A.; Canales, E.; Prasad, K. G. J. Am. Chem. Soc. 2005, 127, 11572-11573.
28. (d) Soderquist, J. A.; Burgos, C. H.; Canales, E.; Matos, K. J. Am. Chem. Soc. 2005, 127, 8044-8049.
29. (e) Chong, J. M.; Wu, T. R.; Shen, L. Org. Lett. 2004, 6, 2701-2704.
30. (f) Woodward, S.; Cunningham, A. Synlett 2002, 43-44.
31. (g) Woodward, S.; Prieto, O. J. Organomet. Chem. 2006, 691, 1515-1519.
32. (h) Woodward, S.; Cunningham, A.; Mokalparekh, V.; Wilson, C. Org. Biomol. Chem. 2004, 2, 741-748.
33. (i) Tietze, L. F.; Kinzel, T.; Schmatz, S. J. Am. Chem. Soc. 2006, 128, 11483-11495.
34. (j) Tietze, L. F.; Völkel, L.; Wulff, C.; Weigand, B.; Bittner, C.; McGrath, P.; Johnson, K.; Schäfer, M. Chem. Eur. J. 2001, 7, 1304-1308.
35. (k) Tietze, L. F.; Weigand, B.; Völkel, L.; Wulff, C.; Bittner, C. Chem. Eur. J. 2001, 7, 161-168.
36. (l) Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem. Eur. J. 1998, 4, 1862-1869.
37. (m) Tietze, L. F.; Wegner, C.; Wulff, C. Eur. J. Org. Chem. 1998, 1639-1644.
38. (n) Tietze, L. F.; Wegner, C.; Wulff, C. Synlett 1996, 471-472.
39. (o) Baba, A.; Yasuda, M.; Kitahara, N.; Fujibayashi, T. Chem. Lett. 1998, 8, 743-744.
40. (p) Miller, J. J.; Sigman, M. S. J. Am. Chem. Soc. 2007, 129, 2752-2753.
41. Wadamoto, M.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 14556-14557.
42. Loh, T. P.; Lu, J.; Hong, M. L.; Ji, S. J.; Teo, Y. C. Chem. Commun. 2005, 4217-4218.
43. Loh, T. P.; Teo, Y. C.; Goh, J. D. Org. Lett. 2005, 7, 2743-2745.
44. For representative examples, see: (a) Wooten, A. J.; Kim, J. G.; Walsh, P. J. Org. Lett. 2007, 9, 381-384.
45. (b) Walsh, P. J.; Kim, J. G.; Waltz, K. M.; Garcia, L. F.; Kwiatkowski, D. J. Am. Chem. Soc. 2004, 126, 12580-12585.
46. (c) Walsh, P. J.; Waltz, K. M.; Gavenonis, J. Angew. Chem. 2002, 114, 3849-3852;
47. Angew. Chem., Int. Ed. 2002, 41, 3697-3699.
48. (d) Tagliavini, E.; Casolari, S.; D'Addario, D. Org. Lett. 1999, 1, 1061-1063.
49. (e) Maruoka, K.; Kii, S. Chirality 2003, 15, 68-70.
50. (f) Maruoka, K.; Hanawa, H.; Kii, S. Adv. Synth. Catal. 2001, 343, 57-60.
51. Shibasaki, M.; Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M. J. Am. Chem. Soc. 2002, 124, 6536-6537.
52. Shibasaki, M.; Wada, R.; Oisak, K.; Kanai, M. J. Am. Chem. Soc. 2004, 126, 8910-8911.
53. For review, see: (a) Chelucci, G.; Murineddu, G.; Pinna, A. G. Tetrahedron: Asymmetry 2004, 15, 1373-1389.
54. (b) Kočovský, P.; Malkov, A. Eur. J. Org. Chem. 2007, 29-36.
55. For achiral and chiral N-oxides acting as Lewis base or organocatalysts catalytic systems. See: (a) He, B.; Chen, F. X.; Feng, X. M.; Zhang, G. L. Tetrahedron Lett. 2004, 45, 5465-5467.
56. (b) Li, Y.; He, B.; Feng, X. M.; Zhang, G. L. Synlett 2004, 1598-1600.
57. (c) Zhou, H.; Chen, F. X.; Qin, B.; Feng, X. M.; Zhang, G. L. Synlett 2004, 1077-1079.
58. (d) Chen, F. X.; Feng, X. M.; Qin, B.; Zhang, G. L.; Jiang, Y. Z. Org. Lett. 2003, 5, 949-952.
59. (e) Shen, Y. C.; Feng, X. M.; Zhang, G. L.; Jiang, Y. Z. Synlett 2002, 1353-1355.
60. (f) Liu, B.; Feng, X. M.; Chen, F. X.; Zhang, G. L.; Cui, X.; Jiang, Y. Z. Synlett 2001, 1551-1554.
61. Wen, Y. H.; Huang, X.; Huang, J. L.; Xiong, Y.; Qin, B.; Feng, X. M. Synlett 2005, 2445-2448.
62. Jiao, Z. G.; Feng, X. M.; Liu, B.; Chen, F. X.; Zhang, G. L.; Jiang, Y. Z. Eur. J. Org. Chem. 2003, 3818-3826.
63. (a) Huang, J. L.; Liu, X. H.; Wen, Y. H.; Qin, B.; Feng, X. M. J. Org. Chem. 2007, 72, 204-208.
64. (b) Huang, X.; Huang, J. L.; Wen, Y. H.; Feng, X. M. Adv. Synth. Catal. 2006, 348, 2579-2584.
65. Qin, B.; Liu, X. H.; Shi, J.; Zheng, K.; Zhao, H. T.; Feng, X. M. J. Org. Chem. 2007, 72, 2374-2378.
66. Li, Q. H.; Chang, L.; Liu, X. H.; Feng, X. M. Synlett 2006, 1675-1678.
67. (a) Li, Q. H.; Liu, X. H; Wang, J.; Shen, K.; Feng, X. M. Tetrahedron Lett. 2006, 47, 4011-4014.
68. (b) Shen, Y. C.; Feng, X. M.; Li, Y.; Zhang, G. L.; Jiang, Y. Z. Eur. J. Org. Chem. 2004, 129-137.
69. Guillaneux, D.; Zhao, S. H.; Samuel, O.; Rainford, D.; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430-9439.
70. Delpech, F.; Guzei, I. A.; Jordan, R. F. Organometallics 2005, 21, 1167-1176.
71. Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2003, 125, 2208-2216.
72. (a) Yasuda, M.; Miyai, T.; Shibata, I.; Baba, A. Tetrahedron Lett. 1995, 36, 9497-9500.
73. (b) Shibata, I.; Kato, H.; Ishida, T.; Yasuda, M.; Baba, A. Angew. Chem. 2004, 116, 729-732;
74. Angew. Chem., Int. Ed. 2004, 43, 711-714.
75. (c) Takita, R.; Fukuta, Y.; Tsuji, R.; Ohshima, T.; Shibasaki, M. Org. Lett. 2005, 7, 1363-1366.