A chiral anisotropic reagent for determination of the absolute configuration of a primary amino compound

Tetrahedron Letters

Volumn 39, Issue 34, 1998, Pages 6245-6248

  Harada, Ken Ichi ^a   Shimizu, Youhei ^a   Fujii, Kiyonaga ^a  

^a MEIJO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 FLUORO 2,4 DINITROPHENYL 5 PHENYLETHYLAMINE; PHENETHYLAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ANISOTROPY; ARTICLE; CHIRALITY; CONFORMATIONAL TRANSITION; DRUG DETERMINATION; HYDROGEN BOND; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0032552160     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01286-6     Document Type: Article

References (11)

1. 1. Kusumi, T.; Fukushima, T.; Ohtani, I.; Kakisawa, H. Tetrahedron Lett. 1991, 32, 2939-2942.
2. 2. Fujii, K.; Ikai, Y.; Oka, H.; Suzuki, M.; Harada, K.-I. Anal. Chem. 1997, 69, 5146-5151.
3. 3. Fujii, K.; Shimoya, T.; Ikai, Y.; Oka, H.; Harada, K.-I. Tetrahedron Lett. 1998, 39, 2579-2582.
4. 4. Fujii, K.; Ikai, Y.; Mayumi, T.; Oka, H.; Suzuki, M.; Harada, K.-I. Anal. Chem. 1997, 69, 3346-3352.
5. 5. Marfey, P. Carlsberg Res. Commun., 1984, 49, 591-596.
6. 3OD) : δ 9.03 (1H, d, J = 8 Hz), δ 7.24-7.27 (5H, m), δ 6.67 (1H, d, J = 14.4 Hz), δ 4.90 (1H, q, 7 = 6.4 Hz), δ 1.67 (3H, d, J = 6.4 Hz).
7. 3 was treated with 1% (R)-FDPEA acetone solution (2 mL (20 mg, 0.0655 mmol)) and the mixture was allowed to stand at 37 °C for 1 hr. After cooling, 1 M HCl (400 μL) was added and the residue obtained after evaporation of the reaction mixture was subjected to preparative TLC (benzene:acetone = 8:2) to give the (R)-FDPEA derivative (9.3 mg, 46%).
8. 8 Okino, T.; Matsuda, H.; Murakami, M.; Yamaguchi, K. Tetrahedron Lett. 1993, 34, 501-504.
9. 2O = 8:1:2 (upper layer) as the mobile phase to give the pure (R)-FDPEA derivative (3.2 mg, 20.9%) and (S)-FDPEA derivative (7.4 mg, 48.4%).
10. 3OD.
11. 12. Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron 1994, 50, 11303-11314.