Synthesis of Chiral Tridentate Ligands Embodying the Bispidine Framework and their Application in the Enantioselective Addition of Diethylzinc to Aldehydes

Abstract:

Several new chiral tridentate ligands with the bispidine moiety were synthesized from N-alkyl bispidines and chiral amino (or hydroxyl) acids. The synthesized ligands were used as catalysts in the enantioselective addition of diethylzinc to several aromatic aldehydes and an aliphatic aldehyde. High yield and enantioselectivity were received in the cases of aromatic aldehydes as substrates especially when the employed chiral ligand has a hydroxyl group attached to the chiral center. The effect of the structure, the amount of tridentate chiral ligands, solvent and temperature on the enantioselectivity of the addition products were studied. A possible mechanism for the addition of diethylzinc to aldehydes in the presence of bispidine-derived ligands were proposed based upon the catalytic reaction results and referred to the mechanisms proposed for other reaction systems in literatures.

• Periodical: Advanced Materials Research (Volumes 396-398)
• Pages: 1236-1243
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.396-398.1236
• Online since: November 2011
• Authors: Yue Cheng Zhang, Jing Yuan Gao, Nai Yue Shi, Ji Quan Zhao
• Keywords: Asymmetric Addition, Benzaldehyde, Bispidine, Chiral Tridentate Ligands, Diethylzinc

References

[1] R. Noyori and M. Kitamura: Angew. Chem. Int. Ed. Engl.Vol. 30 (1991), p.49

[2] L. Pu and H.-B. Yu: Chem. Rev. Vol. 101 (2001), p.757

[3] L. Pu: Tetrahedron. Vol. 59 (2003), p.9873

[4] W.-G. Yang, S. Wu and M. Shi: Chin. J. Org. Chem. Vol. 27 (2007), p.197

[5] R. Noyori: In Asymmetric Catalysis in Organic Synthesis (Wiley, New York 1994).

[6] N. Oguni and T. Omi: Tetrahedron Lett. Vol. 25 (1984), p.2823

[7] D. A. Evans: Science. Vol. 240 (1988), p.420

[8] M. R. Paleo, I. Cabeza and F. J. Sardina: J. Org. Chem. Vol. 65 (2000), p.2108

[9] C. Unaleroglu, A. E. Aydin and A. S. Demir: Tetrahedron: Asymmetry. Vol. 17 (2006), p.742

[10] M. Kitamura, S. Suga and H. Oka: J. Am. Chem. Soc. Vol. 120 (1998), p.9800

[11] M. L. Richmond and C. T. Seto: J. Org. Chem. Vol. 68 (2003), p.7505

[12] H. Sellnerr and D. Seebach: Angew. Chem. Int. Ed. Vol. 38 (1999), p. (1918)

[13] M. Hatano, T. Miyamoto and K. Ishihara: J. Org. Chem. Vol. 71 (2006), p.6474

[14] J. C. Anderson and M. Harding: Chem. Commun. Vol. 3 (1998), p.393.

[15] J. V. Stenhouse: Justus Liebigs Annalen der Chemie. Vol. 78 (1851), p.1

[16] D. J. Gallagher, H. Du, S. A. Long and P. Beak: J. Am. Chem. Soc. Vol. 118 (1996), p.11391

[17] J. T. Bagdanoff and B. M. Stoltz: Angew. Chem. Int. Ed. Vol. 43 (2004), p.353

[18] S. K. Mandal, D. R. Jensen, J. S. Pugsley and M. S. Sigman: J. Org. Chem. Vol. 68 (2003), p.4600

[19] S. E. Denmark, N. Nakajima and O. J. C. Nicaise: J. Am. Chem. Soc. Vol. 116 (1994), p.8797

[20] H. Stetter, J. Schafer and K. Dieminger: Chem. Ber. Vol. 91 (1958), p.598

[21] R. Jeyaraman, S. Avila: Chem. Rev. Vol. 81 (1981), p.149

[22] P. C. Ruenitz and E. E. Smissman: J. Org. Chem. Vol. 42 (1977), p.937

[23] M.-K. Wong, L.-M. Ho, Y.-S. Zheng, C.-Y. Ho and D. Yang: Org. Lett. Vol. 3 (2001), p.2587

[24] A. J. Vernall, S. Ballet and A. D. Abell: Tetrahedron. Vol. 64 (2008), p.3980

[25] N.-Y Shi, J.-Y. Gao, Y.-C. Zhang and J.-Q. Zhao: Chin. J. Org. Chem. Vol. 31 (2011), p.497

[26] G. Blay, I. Fernandez, V. Hernandez-Olmos, A. Marco-Aleixandre and J. R. Pedro: J. Mol. Catal. A-Chem. Vol. 276 (2007), p.235

[27] J. E. D. Martins and M. Wills: Tetrahedron: Asymmetry. Vol. 19 (2008), p.1250

[28] M. Asami, H. Watanabe, K. Honda, and S. Inoue: Tetrahedron: Asymmetry. Vol. 9 (1998), p.4165

[29] J. Spieler, O. Huttenloch and H. Waldmann: Eur. J. Org. Chem. Vol. 3 (2000), p.391

[30] M. Shi, C.-J. Wang: Tetrahedron: Asymmetry. Vol. 13 (2002), p.2161