Determination of the absolute configuration of a secondary alcohol by NMR spectroscopy using difluorodinitrobenzene

Tetrahedron Letters

Volumn 40, Issue 51, 1999, Pages 9081-9084

  Harada, Ken ichi ^a   Shimizu, Youhei ^a   Kawakami, Atsuko ^a   Fujii, Kiyonaga ^a  

^a MEIJO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALPHA METHYLBENZYLAMINE; FLUOROBENZENE;

ANISOTROPY; ARTICLE; CHEMICAL MODIFICATION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS;

EID: 0033579615     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01926-7     Document Type: Article

References (11)

1. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
2. Latypov, S. K.; Seco, J. M.; Quinoá, E.; Riguera, R. J. Org. Chem. 1996, 61, 8569-8577.
3. Latypov, S. K.; Seco, J. M.; Quinoá, E.; Riguera, R. J. Am. Chem. Soc. 1998, 120, 877-882.
4. Harada, K.-I.; Shimizu, Y.; Fujii, K. Tetrahedron Lett. 1998, 39, 6245-6248.
5. Kusumi, T.; Fukushima, T.; Ohtani, I.; Kakisawa, H. Tetrahedron Lett. 1991, 32, 2939-2942.
6. Fujii, K.; Ikai, Y.; Mayumi, T.; Oka, H.; Suzuki, M.; Harada, K.-I. Anal. Chem. 1997, 69, 3346-3352.
7. Approximately 15% NOEs (400 MHz) were observed between the H-6 of FDNB and the α-proton of the secondary alcohol.
8. Approximately 19% and 13% NOEs (400 MHz) were observed between the H-6 of DNB and the Hα of the secondary alcohols tested (linear alcohols and menthol) and the Hα of PEA, respectively. In the case of cholesterol, 12% and 9% NOEs (600 MHz) were observed between the H-6 of DNB and the Hα of the secondary alcohol and the Hα of PEA, respectively.
9. Fujii, K.; Shimoya, T.; Ikai, Y.; Oka, H.; Harada, K.-I. Tetrahedron Lett. 1998, 39, 2579-2582.
10. The NHs of PEA forming the intramolecular hydrogen bonding appear around 8.76 ppm in all secondary alcohols tested in this study.
11. Seco, J. M.; Latypov, S. K.; Quinoá, E.; Riguera, R. Tetrahedron Lett. 1994, 35, 2921-2924.