New chiral ammonium salt hosts derived from amino acids: very efficient optical resolution of 2,2′-dihydroxy-1,1′-binaphthyl by complexation with these host compounds

Abstract

Chiral ammonium salt hosts are prepared from amino acids by transformation of their NH₂ and CO₂H groups into Me₃N⁺Br^- and CH₂OH groups, respectively, via three simple reaction steps; by complexation with these hosts, 2,2′-dihydroxy-1,1′-binaphthyl is resolved very efficiently.

References

1. F. Vogtle, H.-G. Lohr, J. Franke and D. Worsch, Angew. Chem., Int. Ed. Engl., 1985, 24, 727.
2. F. Toda, K. Tanaka, T. Okada, S. A. Bourne and L. R. Nassimbeni, Supramol Chem., 1994, 3, 291.
3. K. Tanaka, K. Tamura and F. Toda, J. Chem. Soc., Perkin Trans. 2, 1995, 1571.
4. K. Tanaka, T. Okada and F. Toda, Angew. Chem., Int. Ed. Engl., 1993, 32, 1147.
5. F. Toda, K. Tanaka, Z. Stein and I. Goldberg, J. Org. Chem., 1994, 59, 5748.
6. F. Toda, K. Tanaka and H. Sawada, J. Chem. Soc., Perkin Trans. 1, 1995, 3065.
7. A. W. Rastou and D. N. Eggenberger, J. Am. Chem. Soc., 1947, 69, 2095.
8. C. C. Tseng, S. Terashima and S. Yamada, Chem. Pharm. Bull., 1977, 25, 29.