Asymmetric synthesis of (R)- and (S)-methyl (2-methoxycarbonylcyclopent-2-enyl)acetate and (R)- and (S)-2-(2-hydroxymethyl-cyclopent-2-enyl)ethanol

Tetrahedron Asymmetry

Volumn 8, Issue 16, 1997, Pages 2683-2685

  Urones, Julio G ^a   Garrido, Narciso M ^a   Diez D ^a   Dominguez, Sara H ^a   Davies, Stephen G ^b  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 HYDROXYMETHYLCYCLOPENT 2 ENYL)ETHANOL; METHYL (2 METHOXYCARBONYLCYCLOPENT 2 ENYL)ACETATE; TERPENE; UNCLASSIFIED DRUG;

ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARTIAL DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030984170     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00340-6     Document Type: Article

References (27)

1. Yamane, T.; Takahashi, M.; Ogasawara, K., Synthesis, 1994, 444.
2. Sakan, T.; Murai, F.; Asoe, S.; Hyeon, S. B.; Hayashi, Y., J. Chem. Soc. Jpn., 1969, 90, 507.
3. (a) Cavill, G. W. K.; Hinterberger, H., Aust. J. Chem. 1960, 13, 514; 1961, 14, 143.
4. (a) Cavill, G. W. K.; Hinterberger, H., Aust. J. Chem. 1960, 13, 514; 1961, 14, 143.
5. (b) Pagnoni, U. M.; Pinetti, A.; Trave, R.; Garanti, C., Aust. J. Chem, 1976, 29, 1375.
6. Sakan, T.; Isoe, S.; Hyeno, S.; Katsumura, R.; Maeda, T.; Wolinsky, J.; Dickerson, D.; Slabaugh, M.; Nelson, D., Tetrahedron Letters, 1965, 3376 and the references cited therein.
7. (a) Uyehara, T.; Shida, N.; Yamamoto, Y., J. Chem. Soc., Chem. Commun, 1989, 113.
8. (b) Uyehara, T.; Shida, N.; Yamamoto, Y., J. Org. Chem., 1992, 57, 3139.
9. Voight, K.; Lansky, A.; Woltemeyer, M.; Meijere, A., Liebigs Ann., 1996, 899.
10. (a) Davies, S. G.; Ichihara, O., Tetrahedron: Asymmetry, 1991, 2, 183.
11. (b) Bunnage, M.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1, 1993, 1375; 1994, 2373.
12. (b) Bunnage, M.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1, 1993, 1375; 1994, 2373.
13. (c) Davies, S. G.; Costello, J. F.; Ichihara, O., Tetrahedron: Asymmetry, 1994, 5, 1999.
14. (d) Davies, S. G.; Walters, I. A. S., J. Chem. Soc. Perkin Trans. I, 1994, 1129.
15. All new compounds were fully characterised including elemental analysis or high resolution mass spectrometry.
16. (a) Davies, S. G.; Garrido, N. M.; Ichihara, O.; Walters, I. A. S., J. Chem. Soc. Chem. Commun., 1993, 1154.
17. (b) Davies, S. G.; Ichihara, O.; Walters, I. A. S., Synlett, 1993, 461.
18. (c) Davies, S. G.; Ichihara, O.; Walters, I. A. S., Synlett, 1994, 117.
19. (d) Davies, S. G.; Walters, I. A. S., J. C. S. Perkin Trans. I, 1994, 1129.
20. (e) Davies, S. G.; Lenoir, I.; Walters, I. A. S., J. C. S. Perkin Trans. I, 1994, 1411.
21. (f) Davies, S. G.; Edwards, A. J.; Walters, I. A. S., Recl. Trav. Chim. Pays-Bas, 1994, 1141.
22. (a) Cope, A. C.; Foster, T. T.; Towle, P. H., J. Am. Chem. Soc., 1949, 71, 3929.
23. (b) Cope, A. C.; Ciganek, E.; Howell, C. F.; Schweizer, E. E., J. Am. Chem. Soc., 1960, 82, 4663.
24. (c) Cram, D. J.; McCarty, J. E., J. Am. Chem. Soc., 1954, 76, 5740.
25. (d) Davies, S. G.; Smyth, G. D., Tetrahedron: Asymmetry, 1996, 7, 1001.
26. (e) Davies, S. G.; Smyth, G. D., J. C. S. Perkin Trans. I, 1996, 2467.
27. 1H NMR analysis of the diester derivatives formed with Mosher's reagent from (R)-2, (S)-2 and racemic.