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

Abstract:

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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.

Info:

Periodical:

Advanced Materials Research (Volumes 518-523)

Edited by:

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

Pages:

266-271

DOI:

10.4028/www.scientific.net/AMR.518-523.266

Citation:

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

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$38.00

[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.

DOI: 10.1002/anie.199100491

[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.

DOI: 10.1016/j.tetasy.2004.10.034

[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.

DOI: 10.1016/j.tetasy.2004.02.013

[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.

DOI: 10.1002/cjoc.20040220604

[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.

DOI: 10.1021/jo00223a019

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