An asymmetric synthesis of (1S, 4R)-4-amino-2-cyclopentenol derivatives

Tetrahedron Letters

Volumn 40, Issue 8, 1999, Pages 1563-1564

  Asami, Masatoshi ^a   Ogawa, Megumi ^a   Inoue, Seiichi ^a  

^a YOKOHAMA NATIONAL UNIVERSITY   (Japan)

Author keywords

Deprotonation; Enantioselection; Epoxides; Rearrangement

Indexed keywords

4 AMINO 2 CYCLOPENTENOL DERIVATIVE; 4 AMINOCYCLOPENTENE OXIDE DERIVATIVE; CYCLOPENTANONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CIS ISOMER; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033582721     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00002-7     Document Type: Article

References (15)

1. O'Brien, P. J. Chem. Soc., Perkin Trans. 1, 1998, 1439-1457 and references therein.
2. (a) Asami, M. J. Synth. Org. Chem., Jpn. 1996, 54, 188-199.
3. (b) Asami, M., Suga, T., Honda, K., Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428.
4. (a) Asami, M. Bull. Chem. Soc. Jpn. 1990, 63, 1402-1408.
5. (b) Asami, M., Takahashi, J., Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649-1652.
6. During the preparation of this manuscript, a reaction of b and lithium (R)-N-methyl-1-phenyl-2-(pyrrolidin-1-yl)ethylamide was reported with moderate selectivity (60%ee): O'Brien, P., Towers, T. D., Voith, M. Tetrahedron Lett. 1998, 39, 8175-8178.
7. (a) Crimmins, M. T. Tetrahedron 1998, 54, 9229-9272.
8. (b) Zhang, D., Miller, M. J. J. Org. Chem. 1998, 63, 755-759.
9. (c) Mulvihill, M. J., Gage, J. L., Miller, M. J. J. Org. Chem. 1998, 63, 3357-3363.
10. A part of this work was reported: Asami, M., Ogawa, M., Honda, K., Inoue, S. The Fifth International Symposium on Carbanion Chemistry, Sendai, Japan, August 1-4, 1998, Abstracts, p 81.
11. Koga, M., Schneller, S. W. Tetrahedron Lett. 1990, 31, 5861-5864.
12. 13C-NMR, IR) data were obtained for these compounds
13. 5c The absolute configuration of 2b was determined tentatively from analogy to 2a.
14. Morley, A. D., Hollinshead, D. M., Procter, G. Tetrahedron Lett. 1990, 31, 1047-1050.
15. Recently an asymmetric synthesis of (R)-4-amino-2-cyclopentenone derivative was reported: Ramesh, N. G., Klunder, A. J. H., Zwanenburg, B. Tetrahedron Lett. 1998, 39, 1429-1432.