Catalytic asymmetric friedel-crafts/protonation of nitroalkenes and N-heteroaromatics

Journal of Organic Chemistry

Volumn 76, Issue 13, 2011, Pages 5450-5456

  Arai, Takayoshi ^a   Awata, Atsuko ^a   Wasai, Makiko ^a   Yokoyama, Naota ^a   Masu, Hyuma ^b  

^a CHIBA UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CU COMPLEXES; FRIEDEL-CRAFTS; NITROALKENES;

ALIPHATIC AMINE; ALKENE DERIVATIVE; AMINOPHENOL; AROMATIC COMPOUND; COPPER; IMIDAZOLINE; INDOLE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; CRYSTALLIZATION; FRIEDEL CRAFTS REACTION; HYPOTHESIS; PROTON TRANSPORT; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

ALKENES; AMINES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, AROMATIC; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITRO COMPOUNDS; PROTONS; STEREOISOMERISM;

EID: 79959653246     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200546a     Document Type: Article

References (50)

1. Dewick, P. M. Medicinal Natural Products: A Biosynthetic Approach; John Wiley & Sons Inc.: Chichester, 2009.
2. Comprehensive Natural Products Chemistry; Cane, D. E., Barton, D. H. R., Nakanishi, K., Meth-Cohn, O., Kelly, J. W., Eds.; Pergamon: New York, 1999.
3. Nichols, D. E.; Lloyd, D. H.; Johnson, M. P.; Hoffman, A. J. J. Med. Chem. 1988, 31, 1406-1412
4. Harada, H.; Hirokawa, Y.; Suzuki, K.; Hiyama, Y.; Oue, M.; Kawashima, H.; Yoshida, N.; Furutani, Y.; Kato, S. Bioorg. Med. Chem. Lett. 2003, 13, 1301-1305
5. Harada, H.; Hirokawa, Y.; Suzuki, K.; Hiyama, Y.; Oue, M.; Kawashima, H.; Kato, H.; Yoshida, N.; Furutani, Y.; Kato, S. Chem. Pharm. Bull. 2005, 53, 184-198
6. Ikunaka, M.; Kato, S.; Sugimori, D.; Yamada, Y. Org. Process Res. Dev. 2007, 11, 73-80
7. Siddiqui, S.; Ahmad, S. S.; Haider, S. I. Tetrahedron Lett. 1987, 28, 1311-1312
8. Vakil, R. J. Circulation 1955, 12, 220-229
9. Selected examples on the synthesis of chiral α-substituted β-indolylalkylamines: Dubois, L.; Mehta, A.; Tourette, E.; Dodd, R. H. J. Org. Chem. 1994, 59, 434-441
10. Boteju, L. W.; Wegner, K.; Qian, X.; Hruby, V. J. Tetrahedron 1994, 50, 2391-2404
11. Bruncko, M.; Crich, D. J. Org. Chem. 1994, 59, 4239-4249
12. Shapiro, G.; Buechler, D.; Marzi, M.; Schmidt, K.; Gomez-Lor, B. J. Org. Chem. 1995, 60, 4978-4979
13. Rodríguez, R.; Viñets, I.; Diez, A.; Rubiralta, M.; Giralt, E. Synth. Commun. 1996, 26, 3029-3059
14. Nenajdenko, V. G.; Karpov, A. S.; Balenkova, E. S. Tetrahedron: Asymmetry 2001, 12, 2517-2527
15. Valdez., S. C.; Leighton, J. L. J. Am. Chem. Soc. 2009, 131, 14638-14639
16. Reviews: Poulsen, T. B; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903-2915
17. Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608-9644
18. You, S.-L.; Cai, Q.; Zeng, M. Chem. Soc. Rev. 2009, 38, 2190-2201
19. Zheng, M.; You, S.-L. Synlett 2010, 1289-1301
20. Racemic synthesis: Bartoli, G.; Bosco, M.; Giuli, S.; Giuliami, A.; Lucarelli, L.; Mercantoni, E.; Sambri, L.; Torregiani, E. J. Org. Chem. 2005, 70, 1941-1944
21. Ballini, R.; Gabrielli, S.; Palmieri, A.; Pereini, M. Tetrahedron 2008, 64, 5435-5441
22. Recent examples of catalytic enantioselective Friedel-Crafts alkylation of indole with nitroalkenes: Bandini, M.; Garelli, A.; Rovinetti, M.; Tommasi, S.; Umani-Ronchi, A. Chirality 2005, 17, 522-529
23. Zhuang, W.; Hazell, R. G.; Jørgensen, K. A. Org. Biomol. Chem. 2005, 3, 2566-2571
24. Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem., Int. Ed. 2005, 44, 6576-6579
25. Fleming, E. M.; McCabe, T.; Connon, S. J. Tetrahedron Lett. 2006, 47, 7037-7042
26. Ganesh, M.; Seidel, D. J. Am. Chem. Soc. 2008, 130, 16464-16465
27. Itoh, J.; Fuchibe, K.; Akiyama, T. Angew. Chem., Int. Ed. 2008, 47, 4016-4018
28. Jia, Y.-X.; Zhu, S.-F.; Yang, Y.; Zhou, Q.-L. J. Org. Chem. 2006, 71, 75-80
29. Lu, S.-F.; Du, D.-M.; Xu, J. Org. Lett. 2006, 8, 2115-2118
30. Yuan, Z.-L.; Lei, Z.-Y.; Shi, M. Tetrahedron: Asymmetry 2008, 19, 1339-1346
31. Liu, H.; Lu, S.-F.; Xu, J.; Du, D.-M. Chem. Asian. J. 2008, 3, 1111-1121
32. Sui, Y.; Liu, L.; Zhao, J.-L.; Wang, D.; Chen, Y.-J. Tetrahedron 2007, 63, 5173-5183
33. Singh, P. K.; Bisai, A.; Singh, V. K. Tetrahedron Lett. 2007, 48, 1127-1129
34. Other approaches for the catalytic asymmetric synthesis of α-substituted β-indolylalkylamines: Wang, X.-F.; Chen, J.-R.; Cao, Y.-J.; Cheng, H.-G.; Xiao, W.-J. Org. Lett. 2010, 12, 1140-1143
35. Zheng, B.-H.; Ding, C.-H.; Hou, X.-L.; Dai, L.-X. Org. Lett. 2010, 12, 1688-1691
36. Dobish, M. C.; Johnston, J. N. Org. Lett. 2010, 12, 5744-5747
37. Enders, D.; Liebich, J. X.; Raabe, G. Chem.-Eur. J. 2010, 16, 9763-9766
38. Arai, T.; Yokoyama, N.; Yanagisawa, A. Chem.-Eur. J. 2008, 14, 2052-2059
39. Yokoyama, N.; Arai, T. Chem. Commun. 2009, 3285-3287
40. Arai, T.; Yokoyama, N. Angew. Chem., Int. Ed. 2008, 47, 4989-4992 Corrigendum: Angew. Chem., Int. Ed. 2010, 49, 9555.
41. Arai, T.; Wasai, M.; Yokoyama, N. J. Org. Chem. 2011, 76, 2909-2912
42. Catalytic asymmetric conjugate additions to nitroacrylates: Zhang, F.-G.; Yang, Q.-Q.; Xuan, J.; Lu, H.-H.; Duan, S.-W.; Chen, J.-R.; Xiao, W.-J. Org. Lett. 2010, 12, 5636-5639
43. Under the current optimized conditions using (S, S, S)- L2 -CuOTf, the reaction of indole and nitrostyrene gave the product in 99% yield with 66% ee (rt, 20 h), though the product was obtained in 99% yield with 72% ee (rt, 5 h) in. (10b)
44. Racemic synthesis: Kusurkar, R. S.; Alkobati, N. A. H. Synth. Commun. 2010, 40, 320-327
45. Enantioselective Friedel-Crafts reaction of pyrrole with nitroalkenes: Trost, B. M.; Müller, C. J. Am. Chem. Soc. 2008, 130, 2438-2439
46. Sheng, Y. -F.; Gu, Q.; Zhang, A.-J.; You, S.-L. J. Org. Chem. 2009, 74, 6899-6901 and also see ref 8j
47. Enantioselective Friedel-Crafts reaction of 4,7-dihydroindoles with nitroalkenes: Sheng, Y.-F.; Li, G.-Q.; Kang, Q.; Zhang, A.-J.; You, S.-L. Chem.-Eur. J. 2009, 15, 3351-3354
48. Takenaka, N.; Chen, J.; Captain, B.; Sarangthem, R. S.; Chandrakumar, A. J. Am. Chem. Soc. 2010, 132, 4536-4537
49. The reaction without (S, S, S)- L2 -CuOTf did not promote the reaction, and the reaction with (S, S, S)- L2 but without CuOTf resulted in a trace amount.
50. A report on the enantioselective Friedel-Crafts/protonation for the α-substituted β-heteroarylnitro adducts: Sibi, M. P.; Coulomb, J.; Stanley, L. M. Angew. Chem., Int. Ed. 2008, 47, 9913-9915