1,2-Dimethyl-3,5-diarylpyrazolidine-4-carboxylic acid derivatives 4a–d were synthesised stereo-selectively via intermolecular [3++2] cycloaddition of aldehydes 1a–d and 1,2-dimethylhydrazine dihydrochloride (2) with ethyl trans-cinnamate (3), stereochemistries of which were assigned by 1H-NOESY spectroscopy, and relative configurations confirmed by X-ray diffraction of one of them (4a).
References
1.
CavallaJ.F., LorkhartI. M., WebbN. E., WinderC. V., WelfordM., and WongA., J. Med. Chem., 1970, 13, 794.
2.
KametaniT., KigasawaK., HiiragiM., WagatsumaN., WakisakaK., SatohF., and SaitoS., J. Med. Chem., 1970, 13, 1064.
3.
TahaA.M., OmarN. M., BayomiS. M., AmmarE. M., and AfifiA., J. Pharm. Sci., 1974, 63, 395.
4.
ShimizuT., HayashiY., MikiM., and TeramuraK., J. Org. Chem., 1987, 52, 2277.
5.
NishinoC., OtakeT., AdachK., and InadaR., Eur. Pat. Appl., EP 736 526, 1996 (Chem. Abstr., 1996, 126, 8112d).
6.
TieccoM., TestaferriL., and MariniF., Tetrahedron, 1996, 52, 11841.
7.
BanuelosL.A., CuadradoP., GonzalezA. M., LopezI., PulidoF. J., and RaithbyP. R., Tetrahedron, 1996, 52, 9193.
8.
OppolzerW., Tetrahedron Lett., 1970, 11, 2199.
9.
ShimizuT., HayashiY., MikiM., and TeramuraK., J. Heterocyclic. Chem., 1990, 27, 1669.
10.
ZlicarM., StanovnikB., and TislerM.Tetrahedron, 1992, 48, 7965.
11.
LefevreG., and HamelinJ., Tetrahedron Lett., 1979, 20, 1757.
12.
LefevreG., SinbandhitS., and HamelinJ., Tetrahedron, 1979, 35, 1821.
13.
LefevreG., and HamelinJ., Tetrahedron, 1980, 36, 887.
14.
HuisgenR., and WeinbergerR., Tetrahedron Lett., 1985, 26, 5119.
15.
SIR92: AltomareA., BurlaM. C., CamalliM., CascaranoM., GiacovazzoC., GuagliardiA., and PolidoriG., J. Appl. Cryst., 1994, 27, 435.
16.
DIRDIF94: BeurskensP. T., AdmiralG., BeurskensG., BosmanW. P., de GelderR., IsraelR., and SmitsJ. M. M., The DIRDIF-94 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1994.
17.
CromerD.T., and WaberJ. T., International Tables for X-ray Crystallography, Kynoch Press, Birmingham, Vol. 4, Table 2.2 A, 1974.
18.
IbersJ.A., and HamiltonM. C., Acta Crystallogr., 1964, 17, 781.
19.
CreaghD.C., and McAuleyW. J., International Tables for Crystallography, ed. WilsonA.J. C., Kluwer Academic Publishers, Boston, Vol. C, Table 4.2.6.8, pp. 219–222, 1992.
20.
CreaghD.C., and HubbellJ. H., International Tables for Crystallography, ed. WilsonA.J. C., Kluwer Academic Publishers, Boston, Vol. C, Table 4.2.4.3, pp. 200–206, 1992.