Reliable assignment of absolute configuration of chiral amines based on the analysis of 1H NMR spectra of their CFTA amide diastereomers

Tetrahedron Asymmetry

Volumn 19, Issue 7, 2008, Pages 847-856

  Fujiwara, Tomoya ^a   Segawa, Masaru ^a   Fujisawa, Hidehito ^a   Murai, Taiki ^a   Takahashi, Tamiko ^a   Omata, Kenji ^b   Kabuto, Kuninobu ^b   Lodwig, Siegfried N ^c   Unkefer, Clifford J ^c   Takeuchi, Yoshio ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c LOS ALAMOS NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALPHA CYANO ALPHA FLUORO 4 TOLYLACETIC ACID; AMIDE; AMINE; AMINO ACID DERIVATIVE; FLUORINE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; MOLECULAR STABILITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 43049124369     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.03.003     Document Type: Article

References (23)

1. Seco J.M., Quiñoá E., and Riguera R. Chem. Rev. 104 (2004) 17-117 and references cited therein
2. Wenzel T., and Wilcox J.D. Chirality 15 (2003) 256-270
3. Dale J.A., Dull D.L., and Mosher H.S. J. Org. Chem. 34 (1969) 2543-2549
4. Dale J.A., and Mosher H.S. J. Am. Chem. Soc. 95 (1973) 512-519
5. Sullivan G.R., Dale J.A., and Mosher H.S. J. Org. Chem. 38 (1973) 2143-2147
6. Dutcher J.S., Macmillan J.G., and Heathcock C.H. J. Org. Chem. 41 (1976) 2663-2669
7. Hietaniemi L., Pohjala E., Malkonen P., and Riekkola M.L. Finn. Chem. Lett. 16 (1989) 67-73
8. Svatos A., Valterova I., Samon D., and Vrkoc J. Collect. Czech. Chem. Commun. 55 (1990) 485-490
9. Takeuchi Y., Itoh N., Kawahara S., and Koizumi T. Tetrahedron 49 (1993) 1861-1870
10. Dale J.A., and Mosher H.S. J. Am. Chem. Soc. 90 (1968) 3732-3738
11. Seco J.M., Latypov S.K., Quiñoá E., and Riguera R. J. Org. Chem. 62 (1997) 7569-7574
12. Takeuchi Y., Segawa M., Fujisawa H., Omata K., Lodwig S.N., and Unkefer C.J. Angew. Chem., Int. Ed. 45 (2006) 4617-4619
13. Takeuchi Y., Itoh N., Note H., Koizumi T., and Yamaguchi K. J. Am. Chem. Soc. 113 (1991) 6318-6320
14. Takeuchi Y., Itoh N., and Koizumi T. J. Chem. Soc., Chem. Commun. (1992) 1514-1515 see also: Chem. Ind. 1992, 874
15. Takeuchi Y., Itoh N., Satoh T., Koizumi T., and Yamaguchi K. J. Org. Chem. 58 (1993) 1812-1820
16. Takeuchi Y., Konishi M., Hori H., Takahashi T., and Kirk K.L. Enantiomer 4 (1999) 339-344
17. Takahashi T., Fukushima A., Taraka Y., Tekeuchi Y., Kabuto K., and Kabuto C. Chem. Commun. (2000) 788-790
18. Takeuchi Y., Fujisawa H., and Noyori R. Org. Lett. 6 (2004) 4607-4610
19. Takeuchi Y., Konishi M., Hori H., Takahashi T., Kometani T., and Kirk K.L. Chem. Commun. (1998) 365-366
20. Fujiwara T., Omata K., Kabuto K., Kabuto C., Takahashi T., Segawa M., and Takeuchi Y. Chem. Commun. (2001) 2694-2695
21. Noe C.R., Knollmuller M., Oberhauser B., Steinbauer G., and Wagner E. Chem. Ber. 119 (1986) 729-743
22. Takeuchi Y., Asahina M., Murayama A., Hori K., and Koizumi T. J. Org. Chem. 51 (1986) 955-956
23. Takeuchi Y., Asahina M., Nagata K., and Koizumi T. J. Chem. Soc., Perkin Trans. 1 (1987) 2203-2207