The configurational assignment of the optically active 5-(1-hydro- peroxyethyl)-3-ethoxycarbonyl-2-methylfuran and its alcohol by exciton- coupled circular dichroism (ECCD)

Tetrahedron Asymmetry

Volumn 8, Issue 21, 1997, Pages 3555-3558

  Adam, Waldemar ^a   Humpf, Hans Ulrich ^a   Korb, Marion N ^a   Schreier, Peter ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; HORSERADISH PEROXIDASE; HYDROPEROXIDE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; PRIORITY JOURNAL; SYNTHESIS;

EID: 0031566706     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00515-6     Document Type: Article

References (13)

1. 1. Adam, W.; Korb, M. N. Tetrahedron: Asymmetry, 1997, 8, 1131-1142.
2. 2. (a) Scettri, A.; Bonadies, F.; Lattanzi, A. Tetrahedron: Asymmetry 1996, 7, 629-632;
3. (b) Lattanzi, A.; Bonadies, F.; Scettri, A. Tetrahedron: Asymmetry, 1997, 8, 2141-2151.
4. 3. (a) Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983;
5. (b) Nakanishi, K.; Berova, N. In Circular Dichroism, Principles and Applications; Nakanishi; K.; Berova, N.; Woody, R. W., Eds; VCH Publishers Inc.; New York, NY. 1994.
6. 4. (a) Gimple, O.; Schreier, P.; Humpf, H.-U. Tetrahedron: Asymmetry 1997, 8, 11-14;
7. (b) Hoch, U.; Humpf, H.-U.; Schreier, P.; Saha-Möller, C. R.; Adam, A. Chirality 1997, 9, 69-74;
8. (c) Schneider, C.; Schreier, P.; Humpf, H.-U. Chirality 1997, in press.
9. 2 (2 mL) were added 1.2 equiv. of 2-naphthoylimidazole (3) or benzoyltriazole (7) and 1.2 equiv. DBU. The reaction mixture was stirred at RT for 2 h, concentrated (20°C/20 Torr) and the product (yield 75-90%) purified by flash chromatography [silica gel, 1:1 petroleum ether (30-35°C):diethyl ether].
10. 3), 6.70 (s, 1 H, C=CH), 7.57 (m, 2 H, H arom.), 7.98 (m, 4 H, H arom.), 8.61 (s, 1 H, H arom.).
11. 7. The π-π* transition of the furan ring is polarized approximately perpendicularly to the C-C axis.
12. 8. Gawronski, J.; Radocki, D. J. Org. Chem. 1990, 55, 1118-1120.
13. 9. Dong, J.-G.; Akritopoulou-Zanze, I ; Guo, J.; Berova, N.; Nakanishi, K.; Harada, N. Enantiomer, 1997, in press.