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An efficient synthetic approach towards a single diastereomer of (2R,3R)-N2,N3-bis((S)-1-phenylethyl)butane-2,3-diamine via metalation and demetalation

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Abstract

A facile synthetic approach has been adopted towards the synthesis of (2R,3R)-N2,N3-bis((S)-1-phenylethyl)butane-2,3-diamine via demetalation of its dichloro Zn(II) complex, which itself was separated from a mixture of diastereomeric Zn(II) complexes by fractional crystallization. The synthesized chiral 1,2-diamine ligand was evaluated as a chiral auxiliary for the Cu(II)-catalysed asymmetric Henry reaction of 3-phenylpropanal and nitromethane, yielding (S)-1-nitro-4-phenylbutan-2-ol in excellent yields (up to 99%) and enantioselectivities (up to 97%).

Graphic abstract

A facile synthetic approach towards (2R,3R)-N2,N3-bis((S)-1-phenylethyl)butane-2,3-diamine (2b) via fractional crystallization and demetalation of its Zn(II) complex has been adopted. 2b served as a highly enantioselective pro-ligand with Cu(OAc)2 for asymmetric Henry reaction of 3-phenylpropanal and nitromethane in the presence of base with 97% > ee and 99% yield.

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Acknowledgements

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF-2017R1D1A3B03030670).

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Authors and Affiliations

  1. Department of Chemistry and Green-Nano Materials Research Center, Kyungpook National University, 1370 Sankyuk-dong, Taegu, 702-701, Republic of Korea

    Juhyun Cho & Jong Hwa Jeong

  2. Department of Chemistry, Shaheed Benazir Bhutto University, Sheringal, Dir (Upper), Khyber Pakhtunkhwa, Pakistan

    Saira Nayab

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  1. Juhyun Cho
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  2. Saira Nayab
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  3. Jong Hwa Jeong
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Correspondence to Saira Nayab or Jong Hwa Jeong.

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Cho, J., Nayab, S. & Jeong, J. An efficient synthetic approach towards a single diastereomer of (2R,3R)-N2,N3-bis((S)-1-phenylethyl)butane-2,3-diamine via metalation and demetalation. Transit Met Chem 45, 9–17 (2020). https://doi.org/10.1007/s11243-019-00351-1

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