NMR determinations of the absolute configuration of α-chiral primary amines

Organic Letters

Volumn 12, Issue 12, 2010, Pages 2856-2859

  Fukui, Hiroki ^a   Fukushi, Yukiharu ^b  

^a AOYAMA GAKUIN UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

AMINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77953565286     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100951s     Document Type: Article

References (33)

1. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy-Exciton Coupling in Organic Stereochemistry; University Science Book: Mill Valley, CA. 1983.
2. Dunitz, J. D. X-Ray Analysis and the Structure of Organic Molecules, 2nd Corrected Reprint; Verlag Helvetica Chimica Acta, Basel and VCH: New York, 1995.
3. Ohtani, I.; Kusumi, T.; Lashman, Y.; Kakisawa, H. J. Org. Chem. 1991, 56, 1296-1298
4. Ohtani, I.; Kusumi, T.; Lashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4093-4096
5. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370-2374
6. Seco, J. M.; Quinoá, E.; Riguera, R. Chem. Rev. 2004, 104, 17-118
7. Fukui, H.; Fukushi, Y.; Tahara, S. Tetrahedron Lett. 1999, 40, 325-328
8. Fukui, H.; Fukushi, Y.; Tahara, S. Tetrahedron Lett. 2003, 44, 4063-4065
9. Fukui, H.; Fukushi, Y.; Tahara, S. Tetrahedron Lett. 2005, 46, 5089-5063
10. Kusumi, T.; Fukushima, T.; Ohtani, I.; Kakisawa, H. Tetrahedron Lett. 1991, 32, 2939-2942
11. Hoye, T. R.; Renner, M. K. J. Org. Chem. 1996, 61, 2056-2064
12. Hoye, T. R.; Renner, M. K. J. Org. Chem. 1996, 61, 8489-8495
13. Hoye, T. R.; Renner, M. K. J. Org. Chem. 2006, 71, 1754
14. Trost, B. M.; Bunt, R. C.; Pully, S. R. J. Org. Chem. 1994, 59, 4202-4204
15. Oshikawa, T.; Yamashita, M.; Kumagai, S.; Seo, K.; Kobayashi, J. J. Chem. Soc., Chem. Commun. 1995, 435-436
16. Chinchilla, R.; Falvello, L. R.; Najera, C. J. Org. Chem. 1996, 61, 7285-7290
17. Seco, J. M.; Latypov, S. K.; E. Quinoá, E.; Riguera, R. J. Org. Chem. 1997, 62, 7569-7574
18. Takeuchi, Y.; Konishi, M.; Hori, H.; Takahashi, T.; Kometani, T.; Kirl, K. L Chem. Commun. 1998, 365-366
19. Latypov, S. K.; Agnov, A. V.; Tahara, S.; Fukushi, Y. Tetrahedron 1999, 55, 7305-7318
20. Takeuchi, Y.; Segawa, M.; Fujisawa, H.; Omata, K.; Lodwig, S. N.; Unkefer, C. J. Angew. Chem., Int. Ed. 2006, 45, 4617-4619
21. Harada, K.; Shimizu, Y.; Fujii, K. Tetrahedron Lett. 1998, 39, 6245-6248
22. Seco, J. M.; E. Quinoá, E.; Riguera, R. J. Org. Chem. 1999, 64, 4669-4675
23. Ahn, H. C.; Choi, K. Org. Lett. 2007, 9, 3853-3855
24. Ahn, H. C.; Choi, K. Chem. Lett. 2007, 36, 1330-1331
25. Tronto, D.; Sarrazin, F.; Pécaut, J.; Marchon, J. -C.; Shang, M.; Scheidt, W. R. Inorg. Chem. 1998, 37, 526-532
26. Lopez, B.; E. Quinoá, E.; Riguera, R. J. Am. Chem. Soc. 1999, 121, 9724-9725
27. Earle, M. A.; Hultin, P. G. Tetrahedron Lett. 2000, 41, 7855-7858
28. Seco, J. M.; Quinoá, E.; Riguera, R. Tetrahedron: Asymmetry 2001, 12, 2915-2925
29. Omata, K.; Fujiwara, T.; Kabuto, K. Tetrahedron: Asymmetry 2002, 13, 1655-1662
30. García, R.; Seco, J. M.; Vázquez, E. S. A.; Quinoá, E.; Riguera, R. J. Org. Chem. 2006, 71, 1119-1130
31. Synthetic detailes are described in SI.
32. Casarini, D.; Lunazzi, L.; Macciantelli, D. J. Chem. Soc., Perkin Trans. 2 1992, 1363-1370
33. Ishikawa, H.; Suzuki, T.; Hayashi, Y. Angew. Chem., Int. Ed. 2009, 48, 1304-1307