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Synthesis of Chiral 1,4,2-Oxazaphosphorinanes Bearing Pyridyl Substituents

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Abstract

A series of 1,4,2-oxazaphosphorinanes was synthesized by the three-component reaction of chiral pyridylcontaining imines with trialkyl phosphites and monochloroacetic acid, followed by dealkylation of the P(O)OAlk-fragments of intermediates. It was established that the major diastereomers of the obtained heterocycles have the same configuration at both chiral centers. The synthesized 1,4,2-oxazaphosphorinanes show catalytic activity in the Friedel–Crafts reaction.

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ACKNOWLEDGMENTS

The measurements have been carried out using the equipment of Distributed Spectral-Analytical Center of Shared Facilities for Study of Structure, Composition and Properties of Substances and Materials of FRC Kazan Scientific Center of RAS.

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Authors and Affiliations

  1. A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Kazan, Russia

    R. G. Zinnatullin, E. K. Badeeva, K. A. Nikitina, K. A. Ivshin, O. N. Kataeva & K. E. Metlushka

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  1. R. G. Zinnatullin
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  2. E. K. Badeeva
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  3. K. A. Nikitina
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  4. K. A. Ivshin
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  5. O. N. Kataeva
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  6. K. E. Metlushka
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Correspondence to K. E. Metlushka.

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To the 145th anniversary of A.E. Arbuzov

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Zinnatullin, R.G., Badeeva, E.K., Nikitina, K.A. et al. Synthesis of Chiral 1,4,2-Oxazaphosphorinanes Bearing Pyridyl Substituents. Russ J Gen Chem 92, 2631–2639 (2022). https://doi.org/10.1134/S1070363222120118

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