Catalytic asymmetric Passerini-type reaction: Chiral aluminum- organophosphate-catalyzed enantioselective α-addition of isocyanides to aldehydes

Journal of Organic Chemistry

Volumn 74, Issue 21, 2009, Pages 8396-8399

  Yue, Tao ^a,b   Wang, Mei Xiang ^a,b   Wang, De Xian ^a,b   Masson, Géraldine ^c   Zhu, Jieping ^c  

^a INSTITUTE OF CHEMISTRY   (China)

^b Tsinghua University   (China)

^c CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC AMOUNTS; CHEMICAL EQUATIONS; CHIRAL LEWIS ACID; ENANTIOSELECTIVE; GOOD YIELD; IN-SITU; ISOCYANIDES;

ACIDS; ALDEHYDES; CHEMICAL REACTIONS; CYANIDES; ENANTIOSELECTIVITY;

CHLORINE COMPOUNDS;

2,2' DIHYDROXY 1,1' BINAPHTHYL; ACETAMIDE DERIVATIVE; ALDEHYDE DERIVATIVE; ALUMINUM DERIVATIVE; CYANIDE; LEWIS ACID; ORGANOPHOSPHATE; OXAZOLE DERIVATIVE;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; ISOLATION PROCEDURE; PASSERINI REACTION; SOLID;

ALDEHYDES; ALUMINUM; CATALYSIS; CYANIDES; MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORIC ACID ESTERS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 70350728705     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9017765     Document Type: Article

References (87)

1. (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
2. (b) Banfi, L.; Riva, R. In Organic Reactions; Overman, L. E., Ed.; Wiley: Hoboken, NJ, 2005; Vol.65, pp 1-140.
3. (c) Marcaccini, S.; Torroba, T. Nat. Protoc. 2007, 2, 632-639.
4. (a) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51-80.
5. (b) Orru, R. V. A.; De Greef, M. Synthesis 2003, 1471-1499.
6. (c) Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899-907.
7. (d) Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144.
8. (e) Dömling, A. Chem. Rev. 2006, 106, 17-89.
9. (f) Tempest, P. Curr. Opin. Drug Discovery Dev. 2005, 8, 776-788.
10. (g) Akritopoulou-Zanze, I.; Djuric, S. W. Heterocycles 2007, 73, 125-147.
11. (h) Isambert, N.; Lavilla, R. Chem. - Eur. J. 2008, 14, 8444-8454.
12. (i) Wessjohann, L. A.; Rivera, D. G.; Vercillo, O. E. Chem. Rev. 2009, 109, 796-814.
13. (j) El Kaim, L.; Grimaud, L. Tetrahedron 2009, 65, 2153-2171.
14. Reviews on enantioselective MCRs: (a) Seayad, J.; List, B. Catalytic Asymmetric Multicomponent Reactions. In Multicomponent reaction; Zhu, J., Bienaymé, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005; pp 277-299.
15. (b) D. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570-1581.
16. (c) Guillena, G.; Ramón, D. J.;Yus, M. Tetrahedron: Asymmetry 2007, 18, 693-700.
17. (d) Gong, L.-Z.; Chen, X.-H.; Xu, X.-Y. Chem.;Eur. J. 2007, 13, 8920-8926.
18. (a) Denmark, S.; Fan, Y. J. Am. Chem. Soc. 2003, 125, 7825-7827.
19. (b) Denmark, S.; Fan, Y. J. Org. Chem. 2005, 70, 9667-9676.
20. Kusebauch, U.; Beck, B.; Messer, K.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 4021-4024.
21. Andreana, P. R.; Liu, C. C.; Schreiber, S. L. Org. Lett. 2004, 6, 4231-4233.
22. Reviews: (a) Larrow, J. F.; Jacobsen, E. N. Top. Organomet. Chem. 2004, 6, 123-152.
23. (b) Katsuki, T. Chem. Soc. Rev. 2004, 33, 437-444.
24. (c) Structure of group 13 compounds incorporating salen ligands: Atwood, D. A.; Harvey, M. J. Chem. Rev. 2001, 101, 37-52.
25. (a) Wang, S. -X.; Wang, M.-X.; Wang, D.-X.; Zhu, J. Angew. Chem., Int. Ed. 2008, 47, 388-391.
26. (b) Yue, T.; Wang, M.-X.; Wang, D.-X.; Zhu, J. Angew. Chem., Int. Ed. 2008, 47, 9554-19457
27. Synthesis of oxazoles from R-isocyanoacetamides: (a) Janvier, P.; Sun, X.; Bienaymé, H.; Zhu, J. J. Am. Chem. Soc. 2002, 124, 2560-2567.
28. (b) Janvier, P.; Bois-Choussy, M.; Bienaymé, H.; Zhu, J. Angew. Chem., Int. Ed. 2003, 42, 811-814.
29. (c) Cuny, G.; Gamez-Montano, R.; Zhu, J. Tetrahedron 2004, 60, 4879-4885.
30. (d) Pirali, T.; Tron, G. C.; Zhu, J. Org. Lett. 2006, 8, 4145-4148.
31. (e) Pirali, T.; Tron, G.; Masson, G.; Zhu, J. Org. Lett. 2007, 9, 5275-5278.
32. (f) Elders, N.; Ruijter, R.; de Kanter, F. J. J.; Groen, M. B.; Orru, R. V. A. Chem. - Eur. J. 2008, 14, 4961-4973.
33. (h) Scheffelaar, R.; Paravidino, M.; Muilwijk, D.; Spek, A. L.; de Kanter, F. J. J.; Orru, R. V. A.; Ruijter, R. Org. Lett. 2009, 11, 125-128.
34. (a) Wang, S.-X.; Wang, M.-X.; Wang, D.-X.; Zhu, J. Org. Lett. 2007, 9, 3615-3618.
35. (b) Wang, S.-X.; Wang, M.-X.; Wang, D.-X.; Zhu, J. Eur. J. Org. Chem. 2007, 4076-4080.
36. Mihara, H.; Xu, Y.; Shepherd, N. E.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 8384-8385.
37. Selected examples: (a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566-1568.
38. (b) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 11804-11805.
39. (c) Rowland, G. B.; Zhang, H.; Rowland, E. B.; Chennamadhavuni, S.; Wang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2005, 127, 15696-15697.
40. (d) Hofmann, S.; Seayad, A. M.; List, B. Angew. Chem., Int. Ed. 2005, 44, 7424-7427.
41. (e) Rueping, M.; Sugiono, E.; Azap, C. Angew. Chem., Int. Ed. 2006, 45, 2617-2619.
42. (f) Storer, R. I.; Carrera, D. E.; Ni, D.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84-86.
43. (g) Chen, X.-H.; Xu, X.-Y.; Liu, H.; Cun, L.-F.; Gong, L.-Z. J. Am. Chem. Soc. 2006, 128, 14802-14803.
44. (h) Kang, Q.; Zhao, Z.-A.; You, S.-L. J. Am. Chem. Soc. 2007, 129, 1484-1485.
45. (i) Jia, Y.-X.; Zhong, J.; Zhu, S.-F.; Zhang, C.-M.; Zhou, Q. L. Angew. Chem., Int. Ed. 2007, 46, 5565-5567.
46. (j) Wanner, M. J.; van der Haas, R. N. S.; de Cuba, K. R.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem., Int. Ed. 2007, 46, 7485-7487.
47. (k) Sickert, M.; Schneider, C. Angew. Chem., Int. Ed. 2008, 47, 3631-3634.
48. (l) Baudequin, C.; Zamfir, A.; Tsogoeva, S. B. Chem. Commun. 2008, 4637-4639.
49. (m) Enders, D.; Narine, A. A.; Toulgoat, F.; Bisschops, T. Angew. Chem., Int. Ed. 2008, 47, 5661-5665.
50. (n) Xu, S.; Wang, Z; Zhang, X.; Zhang, X.; Ding, K. Angew. Chem., Int. Ed. 2008, 47, 2840-2843.
51. (o) Jiang, J.; Yu, J.; Sun, X.-X.; Rao, Q.-Q.; Gong, L.-Z. Angew. Chem., Int. Ed. 2008, 47, 2458-2462.
52. (p) Cheng, X.; Goddard, R.; Buth, G.; List, B. Angew. Chem., Int. Ed. 2008, 47, 5079-5081.
53. (q) Guo, Q.-S.; Du, D.-M.; Xu, J. Angew. Chem., Int. Ed. 2008, 47, 759.
54. (r) Rueping, M.; Antonchick, A. P.; Sugiono, E.; Grenader, K. Angew. Chem., Int. Ed. 2009, 48, 908-910.
55. (s) Liu, H.; Dagousset, G.; Masson, G.; Zhu, J. J. Am. Chem. Soc. 2009, 131, 4598-4599.
56. (t) Terada, M.; Machioka, K.; Sorimachi, K. Angew. Chem., Int. Ed. 2009, 48, 2553-2556.
57. (u) Akiyama, T.; Suzuki, T.; Mori, K. Org. Lett. 2009, 11, 2445-2447.
58. (a) Akiyama, T. Chem. Rev. 2007, 107, 5744-5758.
59. (b) Terada, M. Chem. Commun. 2008, 4097-4112.
60. (c) Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713-5743.
61. (a) Nakashima, D.; Yamamoto, H. J. Am. Chem. Soc. 2006, 128, 9626-9627.
62. (b) Rueping, M.; Ieawsuwan, W.; Antonchick, A. P.; Nachtsheim, B. J. Angew. Chem., Int. Ed. 2007, 46, 2097-2100.
63. (c) Rueping, M.; Nachtsheim, B. J.; Moreth, S. A.; Bolte, M. Angew. Chem., Int. Ed. 2008, 47, 593-596.
64. (d) Terada, M.; Soga, K.; Momiyama, N. Angew. Chem., Int. Ed. 2008, 47, 4122-4125.
65. (e) Garcia-Garcia, P.; Lay, F.; Garcia-Garcia, P.; Rabalakos, C.; List, B. Angew. Chem., Int. Ed. 2009, 48, 4363-4366.
66. The R-isocyanoacetamides are easily available, see: (a) Fayol, A.; Housseman, C.; Sun, X.; Janvier, P.; Bienaymé, H.; Zhu, J. Synthesis 2005, 161-165.
67. (b) Housseman, C.; Zhu, J. Synlett 2006, 1777-1779.
68. (c) Dömling, A.; Beck, B.; Fuchs, T.; Yazbak, A. J. Comb. Chem. 2006, 8, 872-880.
69. For phosphoric acids- and phosphinic acids-catalyzed Ugi-type reactions, see: (a) Pan, S. C.; List, B. Angew. Chem., Int. Ed. 2008, 47, 3622-3625.
70. (b) Yue, T.; Wang, M.-X.; Wang, D.-X.; Masson, G.; Zhu, J. Angew. Chem., Int. Ed. 2009, 48, 6717-6721.
71. (a) Jin, X. L.; Sugihara, H.; Daikai, K.; Tateishi, H.; Jin, Y. Z.; Furono, H.; Inanaga, J. Tetrahedron 2002, 58, 8321-8329.
72. (b) Furono, H.; Hayano, T.; Kambara, T.; Sugimoto, Y.; Hanamoto, T.; Tanaka, Y.; Jin, Y. Z.; Kagawa, T.; Inanaga, J. Tetrahedron 2003, 59, 10509-10523.
73. (c) Suzuki, S.; Furono, H.; Yokoyama, Y.; Inanaga, J. Tetrahedron: Asymmetry 2006, 17, 504-507.
74. Using phosphoric acid 4i as ligand gave non-reproducible results, presumably due to the interaction between the nitro group and aluminium. The reaction was preferably performed at 0.05 M instead of 0.07 M for the solubility issue.
75. 2AlMe, see: (a) Itoh, A.; Oshima, K.; Yamamoto, H.; Nozaki, H. Bull. Chem. Soc. Jpn. 1980, 53, 2050-2054.
76. (b) Hashimoto, S.; Itoh, A.; Kitagawa, Y.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 4192-4194.
77. Selected examples: (a) Fayol, A.; Zhu, J. Angew. Chem., Int. Ed. 2002, 41, 3633-3635.
78. (b) Janvier, P.; Bienaymé, H.; Zhu, J. Angew. Chem., Int. Ed. 2002, 41, 4291-4294.
79. (c) Gámez-Montaño, R.; González-Zamora, E.; Potier, P.; Zhu, J. Tetrahedron 2002, 58, 6351-6358.
80. (d) Fayol, A.; Zhu, J. Org. Lett. 2005, 7, 239-242.
81. (e) Bughin, C.; Masson, G.; Zhu, J. J. Org. Chem. 2007, 72, 1826-1829.
82. (f) Bonne, D.; Dekhane, M.; Zhu, J. Angew. Chem., Int. Ed. 2007, 46, 2485-2488.
83. For reviews on the chemistry of oxazole see: (a) Karpeiskii, M. Y.; Florent'ev, V. L. Russ. Chem. Rev. 1969, 38, 540-546.
84. (b) Jacobi, P. A. Adv. Heterocycl. Nat. Prod. Synth. 1992, 2, 251-298.
85. (c) Yeh, V. S. C. Tetrahedron 2004, 60, 11995-12042.
86. For reviews on Al-Binol complex catalyzed asymmetric reactions, see: (a) Wulff, W. D. Chiral aluminium Lewis acids in organic synthesis. In Lewis acids in organic synthesis; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, Germany, 2000; pp 283-354.
87. (b) Gröger, H. Chem. - Eur. J. 2001, 7, 5247-5251.