A short asymmetric synthesis of 2,5-disubstituted pyrrolidines

Tetrahedron Letters

Volumn 39, Issue 13, 1998, Pages 1697-1700

  Katritzky, Alan R ^a   Cui, Xi Lin ^a   Yang, Baozhen ^a   Steel, Peter J ^b  

^a University of Florida ^*  (United States)

^b UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; DRUG SYNTHESIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0032568229     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00134-8     Document Type: Article

References (12)

1. 1. Higashiyama, K.; Inoue, H.; Takahashi, H. Tetrahedron 1994, 50, 1083.
2. 2. Shiosaki, K.; Rapoport, H. J. Org. Chem. 1985, 50, 1229.
3. 3. Oppolzer, W.; Bochet, C. G.; Merifield, E. Tetrahedron Lett. 1994, 35, 7015.
4. 4. Machinaga, N.; Kibayashi, C. J. Org. Chem. 1991, 56, 1386.
5. 5. Arseniyadis, S.; Huang, P. Q.; Husson, H.-P. Tetrahedron Lett. 1988, 29, 631.
6. 6. Huang, P. Q.; Arseniyadis, S.; Husson, H.-P. Tetrahedron Lett. 1987, 28, 547.
7. 4O: C, 70.55; H, 5.93; N, 18.30. Found: C, 70.16; H, 6.18; N, 18.23.
8. -1, 3082 reflections, 209 parameters, R = 0.0331, wR = 0.0763 for all data.
9. 9. Katritzky, A. R.; Lan, X.; Yang, Z. J.; Denisko, O. V. Chem. Rev. 1997, in press.
10. -1, 1246 reflections, 149 parameters, R = 0.0385, wR = 0.1038 for all data.
11. 4. After removal of the solvent, the residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate = 10/1), to give pure products 5 and 6.
12. 3 and hexane gave crystalline products.