The Synthesis of Novel Chiral Ferrocenyl Aziridino Alcohol Ligands with Two Stereogenic Carbons and Structural Characteristics


Article Preview

L-threonine (2S,3S) was obtained from easily available L-threonine (2S,3R) after four steps,then seven chiral ligands 9a-9g were prepared by the esterification,condensation,reductive alkylation,cyclization,then reduction with treatment with RMgX.All seven kinds of novel compounds were characterized by 1HNMR,13CNMR,IR and HRMS.Compound 9a was further characterized by X-ray diffraction.The X-ray structure analysis revealed that an intermolecular hydrogen bond is present.



Advanced Materials Research (Volumes 518-523)

Edited by:

Reza Iranpour, Ji Zhao, Aijie Wang, Fenglin Yang and Xinyong Li




Q. Wang et al., "The Synthesis of Novel Chiral Ferrocenyl Aziridino Alcohol Ligands with Two Stereogenic Carbons and Structural Characteristics", Advanced Materials Research, Vols. 518-523, pp. 266-271, 2012

Online since:

May 2012




[1] Noyori, R.; Kitamura, M. Enantioselective Addition of Organometallic Reagents to Carbonyl Compounds: chirality transfer, Multiplication and Amplifacation. Angew. Chem. Int. Ed. Engl Vol. 30(1991), pp.49-69.


[2] Wang, M. C.; Liu, L. T.; Zhang, J. S.; Shi, Y. Y.; Wang, D. K. Synthesis of chiral ferrocenyl aziridino alcohols and use in the catalytic asymmetric addition of diethylzinc to aldehydes. Tetrahedron: Asymmetry Vol. 15(2004), pp.3853-3859.


[3] Wang, M. C. ; Wang, D, K,; Zhu, Y; Liu, L. T.; Guo, Y, F. Enantiopure N- ferrocenyl methylaziridin-2-ylmethanols from l-serine: synthesis, crystal structure and applications. Tetrahedron: Asymmetry Vol. 15(2004), p.1289.


[4] Wang, M. C.; Wang, D. K.; Lou, J. P.; Hua, Y. Z. Novel Chiral Ferrocenyl Aziridino Alcohol Catalysts Promoting Asymmetric Addition of Diethylzinc to Aldehydes. Chinese Journal of Chemisty Vol. 22(2004), pp.512-514.


[5] Thompson, C .M.; Frick, J. A.; Green, D. L. C. Synthesis, Configuration, and Chemical Shift Correlations of Chrial 1, 3, 2. -oxazaphos- pholidinz derived from 1-serine. J. Org. Chem. Vol. 55(1990), p.111.

[6] Kenneth. J.; Luly. et al. Routes to Mitomycins, Chirospecific Synthesis of Aziridinomitosenes. J. Org. Chem. Vol. 50(1985), pp.4515-4523.