Gamze KOZ, Demet ASTLEY, Stephen Thomas ASTLEY

Enantioselective Henry reaction catalyzed by a novel L-(+)-aspartic acid-derived Schiff base ligand and Cu(II) ion

Mild and efficient enantioselective Henry reactions of nitromethane with various aldehydes were catalyzed by a novel L-(+)-aspartic acid-derived Schiff base ligand in the presence of Cu(II) ions, affording the corresponding adducts in high yields (up to 96%) and enantioselectivities (up to 92% ee).

Anahtar Kelimeler:

Enantioselective Henry reaction, chiral Schiff base, L-(+)-aspartic acid

Enantioselective Henry reaction catalyzed by a novel L-(+)-aspartic acid-derived Schiff base ligand and Cu(II) ion

Keywords:

Enantioselective Henry reaction, chiral Schiff base, L-(+)-aspartic acid,

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1. Rosini, G. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon, Oxford, UK, 1999.
2. Ono, N. The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001.
3. Luzzio, F. A. Tetrahedron 2001, 57, 915-945.
4. (a) Asai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420; (b) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368-1372; (c) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210; (d) Sasai, H.; Watanabe, S.; Suzuki, T.; Shibasaki, M. Org. Synth. 2004, 10, 571-575; (e) Purkarthofer, T.; Gruber, K.; Gruber-Khadjawi, M.; Waich, K.; Skranc, W.; Mink, D.; Griengl, H. Angew. Chem. Int. Ed. 2006, 118, 3532-3535.
5. (a) Trost, B. M.; Yeh, V. S. C. Angew. Chem. Int. Ed. 2002, 114, 889-891; (b) Trost, B. M.; Yeh, V. S. C.; Ito, H.; Bremeyer, N. Org. Lett. 2002, 4, 2621-2623