Highly enantioselective Henry (nitroaldol) reaction of aldehydes and α-ketoesters catalyzed by N,N′-dioxide-copper(I) complexes

Journal of Organic Chemistry

Volumn 72, Issue 24, 2007, Pages 9323-9328

  Qin, Bo ^a   Xiao, Xiao ^a   Liu, Xiaohua ^a   Huang, Jinglun ^a   Wen, Yuehong ^a   Feng, Xiaoming ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL SPACE; HENRY (NITROALDOL) REACTION; QUATERNARY CARBON;

CARBON; CATALYST ACTIVITY; COPPER COMPOUNDS; ENANTIOSELECTIVITY; ESTERS; LIGANDS; NUCLEAR MAGNETIC RESONANCE;

ALDEHYDES;

ALDEHYDE DERIVATIVE; ALPHA KETOESTER DERIVATIVE; COPPER COMPLEX; ESTER DERIVATIVE; OXIDE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; MASS SPECTROMETRY; OPTICAL ROTATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

ALDEHYDES; ALGORITHMS; CATALYSIS; COPPER; ESTERS; KETONES; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; NITRO COMPOUNDS; ORGANOMETALLIC COMPOUNDS; OXIDES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 36649037582     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701898r     Document Type: Article

References (69)

1. For review of the chiral ligand design, see: (a) Desimoni, G.; Faita, G.; Jørgensen, K. A. Chem. Rev. 2006, 106, 3561-3651.
2. (b) Arrayas, R. G.; Adrio, J.; Carretero, J. C. Angew. Chem., Int. Ed. 2006, 45, 7674-7715.
3. (c) Fonseca, M. H.; König, B. Adv. Synth. Catal. 2003, 345, 1173-1185.
4. For review of chiral N-oxide, see: (a) Malkov, A. V.; Kočovský, P. Eur. J. Org. Chem. 2007, 29-36.
5. (b) Chelucci, G.; Murineddu, G.; Pinna, G. A. Tetrahedron: Asymmetry 2004, 15, 1373-1389.
6. (a) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419-6420.
7. (b) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799-2801.
8. (c) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kočovský, P. Org. Lett. 2002, 4, 1047-1049.
9. (d) Malkov, A. V.; Dufková, L.; Farrugia, L.; Koč ovský, P. Angew. Chem., Int. Ed. 2003, 42, 3674-3677.
10. (e) Pignataro, L.; Benaglia, M.; Annunziata, R.; Cinquini, M.; Cozzi, F. J. Org. Chem. 2006, 71, 1458-1463.
11. (f) Traverse, J. F.; Zhao, Y.; Hoveyda, A. H.; Snapper, M. L. Org. Lett. 2005, 7, 3151-3154.
12. (a) Shen, Y. C.; Feng, X. M.; Li, Y.; Zhang, G. L.; Jiang, Y. Z. Eur. J. Org. Chem. 2004, 129-137.
13. (b) Saito, M.; Nakajima, M.; Hashimoto, S. Chem. Commun. 2000, 1851-1852.
14. (c) Nakajima, M.; Yamamoto, S.; Yamaguchi, Y.; Nakamura, S.; Hashimoto, S. Tetrahedron 2003, 59, 7307-7313.
15. (d) Wong, W. L.; Lee, W. S.; Kwong, H. L. Tetrahedron: Asymmetry 2002, 13, 1485-1492.
16. (e) Dyker, G.; Hölzer, B.; Henkel, G.; Tetrahedron: Asymmetry 1999, 10, 3297-3307.
17. (f) Derdau, V.; Laschat, S.; Hupe, E.; König, W. A.; Dix, I.; Jones, P. G. Eur. J. Inorg. Chem. 1999, 1001-1007.
18. (g) Kerr, W. J.; Lindsay, D. M.; Rankin, E. M.; Scott, J. S.; Watson, S. P. Tetrahedron Lett. 2000, 41, 3229-3233.
19. (a) Zhang, X.; Chen, D. H.; Liu, X. H.; Feng, X. M. J. Org. Chem. 2007, 72, 5227-5233.
20. (b) Zheng, K.; Qin, B.; Liu, X. H.; Feng, X. M. accepted by J. Org. Chem. 2007, 72, 8478-8483.
21. (c) Li, Q. H.; Liu, X. H.; Wang, J.; Shen, K.; Feng, X. M. Tetrahedron Lett. 2006, 47, 4011-4014.
22. (d) Li, Q. H.; Chang, L.; Liu, X. H.; Feng, X. M. Synlett 2006, 1675-1678.
23. Henry, L. C. R. Hebd. Seances. Acad. Sci. 1895, 120, 1265-1268.
24. For reviews for the Henry (nitroaldol) reaction, see: (a) Palomo, C.; Oiarbide, M.; Laso, A. Eur. J. Org. Chem. 2007, 2561-2574.
25. (b) Palomo, C.; Oiarbide, M.; Mielgo, A. Angew. Chem., Int. Ed. 2004, 43, 5442-5444.
26. (c) Boruwa, J.; Gogoi, N.; Saikia, P. P.; Barua, N. C. Tetrahedron: Asymmetry 2006, 17, 3315-3326.
27. (a) Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
28. (b) Rosini, G. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: New York, 1991; pp. 321-340.
29. (c) Luzzio, F. A. Tetrahedron 2001, 57, 915-945.
30. (a) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420.
31. (b) Sasai, H.; Suzuki, T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854.
32. (c) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373.
33. (a) Iseki, K.; Oishi, S.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 9081-9084.
34. (b) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368-1372.
35. (c) Saá, J. M.; Tur, F.; González, J.; Vega, M.; Tetrahedron: Asymmetry 2006, 17, 99-106.
36. (d) Trost, B. M.; Yeh, V. S. C.; Angew. Chem., Int. Ed. 2002, 41, 861-863.
37. (e) Trost, B. M.; Yeh, V. S. C.; Ito, H.; Bremeyer, N. Org. Lett. 2002, 4, 2621-2623.
38. (f) Zhong, Y. W.; Tian, P.; Lin, G. Q. Tetrahedron: Asymmetry 2004, 15, 771-776.
39. (g) Gao, J.; Martell, A. E. Org. Biomol. Chem. 2003, 1, 2801-2806.
40. (h) Palomo, C.; Oiarbide, M.; Laso, A. Angew. Chem., Int. Ed. 2005, 44, 3881-3884.
41. (i) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692-12693.
42. (j) Du, D. M.; Lu, S. F.; Fang, T.; Xu, J. J. Org. Chem. 2005, 70, 3712-3715.
43. (k) Gan, C.; Lai, G.; Zhang, Z.; Wang, Z.; Zhou, M. M. Tetrahedron: Asymmetry 2006, 17, 725-728.
44. (l) Blay, G.; Climent, E.; Fernández, I.; Hernandez-Olmos, V.; Pedro, J. R. Tetrahedron: Asymmetry 2006, 17, 2046-2049.
45. (m) Maheswaran, H.; Prasanth, K. L.; Krishna, G. G.; Ravikumar, K.; Sridhar, B.; Kantam, M. L. Chem. Commun. 2006, 4066-4068.
46. (n) Arai, T.; Watanabe, M.; Fujiwara, A.; Yokoyama, N.; Yanagisawa, A. Angew. Chem., Int. Ed. 2006, 45, 5978-5981.
47. (o) Ma, K.; You, J. Chem. Eur. J. 2007, 13, 1863-1871.
48. (p) Xiong, Y.; Wang, F.; Huang, X.; Wen, Y. H.; Feng, X. M. Chem. Eur. J. 2007, 13, 829-833.
49. (q) Lu, S.-F; Du, D.-M; Zhang, S.-W; Xu, J. Tetrahedron: Asymmetry 2004, 15, 3433-3441.
50. (a) Ooi, T.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 2054-2055.
51. (b) Risgaard, T.; Gothelf, K. V.; Jørgensen, K. A. Org. Biomol. Chem. 2003, 1, 153-156.
52. (a) Chinchilla, R.; Nájera, C.; Sánchez-Agulló, P. Tetrahedron: Asymmetry 1994, 5, 1393-1402.
53. (b) Allingham, M. T.; Howard-Jones, A.; Murphy, P. J.; Thomas, D. A.; Caulkett, P.W. R. Tetrahedron Lett. 2003, 44, 8677-8680.
54. (c) Sohtome, Y.; Hashimoto, Y.; Nagasawa, K. Adv. Synth. Catal. 2005, 347, 1643-1648.
55. (d) Sohtome, Y.; Hashimoto, Y.; Nagasawa, K. Eur. J. Org. Chem. 2006, 2894-2897.
56. (e) Marcelli, T.; van der Haas, R. N. S.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem., Int. Ed. 2006, 45, 929-931.
57. Choudary, B. M.; Ranganath, K. V. S.; Pal, U.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2005, 127, 13167-13171.
58. (a) Ma, J. A.; Cahard, D. Angew. Chem., Int. Ed. 2004, 43, 4566-4583.
59. (b) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210.
60. (c) Gröger, H. Chem. Eur. J. 2001, 7, 5246-5251.
61. (d) Rowlands, G. J. Tetrahedron 2001, 57, 1865-1882.
62. (a) Christensen, C.; Juhl, K.; Jørgensen, K. A. Chem. Commun. 2001, 2222-2223.
63. (b) Christensen, C.; Juhl, K.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 4875-4881.
64. (c) Li, H.; Wang, B.; Deng, L. J. Am. Chem. Soc. 2006, 128, 732-733.
65. (e) Mandal, T.; Samanta, S.; Zhao, C. G. Org. Lett. 2007, 9, 943-945.
66. (a) Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533-3539.
67. (b) Balahura, R. J.; Jordan, R. B. J. Am. Chem. Soc. 1970, 92, 1533-1539.
68. (c) Fairlie, D. P.; Angus, P. M.; Fenn, M. D.; Jackson, W. G.; Inorg. Chem. 1991, 30, 1564-1569.
69. (d) Antolovich, M.; Phillips, D. J.; Rae, A. D. Inorg. Chim. Acta 1989, 156, 189-193.