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Journal of the Iranian Chemical Society

, Volume 16, Issue 3, pp 583–591 | Cite as

Asymmetric synthesis of α-bromohydrins by carrot root as biocatalyst and conversion to enantiopure β-hydroxytriazoles and styrene oxides using click chemistry and SN2 ring-closure

  • Rahman HosseinzadehEmail author
  • Maryam Mohadjerani
  • Sakineh Mesgar
Original Paper
  • 63 Downloads

Abstract

In this study we have combined the bioreduction of α-bromoketones using carrot root as biocatalyst and click chemistry for the preparation of enantiopure β-hydroxytriazoles in excellent enantiomeric excesses and yields. Moreover, we have utilized chiral α-halohydrins for the synthesis of enantiopure styrene oxides in very good yields and enantiomeric excesses. Structural assignments of the products were based on their 1H and 13C NMR data and their optical rotations. The enantiomeric excess of the chiral products was obtained by HPLC analysis.

Keywords

Bioreduction Biocatalyst Carrot root Chiral α-halohydrins Chiral β-hydroxytriazoles Chiral styrene oxides 

Notes

Acknowledgements

Financial support of this work from the Research Council of University of Mazandaran is gratefully acknowledged.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

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Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  1. 1.Department of Organic Chemistry, Faculty of ChemistryUniversity of MazandaranBabolsarIran
  2. 2.Department of Molecular and Cell Biology, Faculty of Basic ScienceUniversity of MazandaranBabolsarIran

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