Abstract
Three 3,4-dihydroxy-2,5-bis-(2′-(4′-substituted-oxazolinyl)) furans were synthesized at 90%–94% yields from reaction of 3,4-dihydroxyfuran-2,5-dicar-boxylic acid or its dimethyl ester with chiral β-amino alcohol via a one-step process. Their chemical structures were determined by 1H NMR, IR, MS, and elemental analysis. With these chiral bisoxazoline ligands, the asymmetric reductive reaction of β-acetonaphthalene with KBH4 or NaBH4 was preliminarily studied. The enantiomeric excess of the reduction product was up to 83.2% with cyclohexane as the solvent, the molar ratio of ligand: reductive agent: β-acetonaphthalene is 0.04:1.6:1, and 72-hours reaction time at 0°C. Furancontaining bisoxazoline with 4-benzyl on oxazoline rings exhibited higher enatioselectivity than congeneric bisoxazolines with 4-ethyl on oxazoline rings.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Butula I., Karlovic G., Catalytic Hydrogenation of nitrogen containing heterocycles, IV. Hydrogenolysis of bridged oxalozines and oxazolidines, Liebigs Ann. Chem., 1976, 7–8: 1455–1464
Ghosh A. K., Mathivanan P., Cappoello J., C2-symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis, Tetrahedron: Asymmetry, 1998, 9: 1–45
Gomez M., Muller G., Rocamora M., Coordination chemistry of oxazoline ligands, Coord. Chem. Rev., 1999, 193–195: 769–835
Glorius F., Pfaltz A., Enantioselective molybdenum-catalyzed allylic alkylation using chiral bisoxazoline ligands, Org. Lett., 1999, 1(11): 141–144
Mazet C., Gade L. H., Charging and deforming the pybox ligand: Enantiomerically pure double helices and their interconversion, Chem. Eur. J., 2002, 8(18): 4308–4318
Desimon G., Faita G., Quadrellip P., Pyridine-2,6-bis(oxazoline). Helpful ligands for asymmetric catalysts, Chem. Rev., 2003, 103: 3119–3154
Corey E. J., Imai N., Zhang H. Y., Designed catalyst for enantioselective Diels-Alder addition from a C2-symmetric chiral bis(oxazoline)-Fe (III) complex, J. Am. Chem. Soc., 1991, 113: 728–729
Davies I. W., Gerena L., Lu N., Larsen R.D. and Reider P.J., Concise synthesis of conformationally constrained pybox ligands, J. Org. Chem., 1996, 61(26): 9629–9630
Andrus M. B., Asgari D., Asymmetric allylic oxidation with biarybisoxazolines-copper (1) catalysis, Tetrahedron, 2000, 56: 5775–5780
Ammar H. B., Notre L. J., Salem M., Kaddachi M.T. and Dixneuf P.H., Synthesis of bis-oxazoline-ruthenium (II)-arene complexes: Combined catalytic isomerisation and Claisen rearrangement of bis-allyl ether, J. Organomet. Chem., 2002, 662: 63–69
Bayardon J., Sinou D., Fluorous chiral bisoxazolines. Synthesis and applications to an asymmetric allylic alkylation, Tetrahedron Lett., 2003, 44: 1449–1451
Kato K., Tanaka M., Yamamura S., Yamamoto Y. and Akita H., Asymmetric cyclization-carbonylation of 2-propargyl-1,3-diones, Tetrahedron Lett., 2003, 44: 3089–3092
Boulch R., Scheurer A., Mosset P. and Saalfrank R.W., Asymmetric cyclopropanation catalyzed by C 2-symmetric bis (oxazolines), Tetrahedron Lett., 2000, 41: 1023–1026
Hofmann A. A., Eugster C. H., 3,4-Dimethoxyfuran: Eigenschaften, berechnungen und substitutionsreaktionen, Helv. Chim. Acta, 1978, 61(1): 430–443
Abiko A., Masamune S., An improved, convenient procedure for reduction of amino acids to aminoalcohols: Use of NaBH4-H2SO4, Tetrahedron Lett., 1992, 33(38): 5517–5518
Aldrich, Handbook of Fine Chemicals and Laboratory Equipment, USA, 2003–2004, 1134
Author information
Authors and Affiliations
Additional information
__________
Translated from Chinese Journal of Applied Chemistry, 2005, 22(12) (in Chinese)
About this article
Cite this article
Li, W., Xu, Z. Synthesis and applications of 3,4-dihydroxy-2,5-bis-(2′-(4′-substituted-oxazolinyl)) furan. Front. Chem. China 1, 292–295 (2006). https://doi.org/10.1007/s11458-006-0035-8
Issue Date:
DOI: https://doi.org/10.1007/s11458-006-0035-8