A noncovalent hybrid of [Pd(phen)(OAc)2] and st-DNA for the enantioselective hydroamination of β-nitrostyrene with methoxyamine

Mrityunjoy Pal; Dulal Musib; Maynak Pal; Gopal Rana; Gobinda Bag; Subrata Dutta; Mithun Roy

doi:10.1039/D1OB00714A

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A noncovalent hybrid of [Pd(phen)(OAc)₂] and st-DNA for the enantioselective hydroamination of β-nitrostyrene with methoxyamine†‡

Mrityunjoy Pal,^a Dulal Musib,^a Maynak Pal,^a Gopal Rana,^b Gobinda Bag,^a Subrata Dutta^c and Mithun Roy

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, National Institute of Technology Manipur, Langol, Imphal, Manipur, India
E-mail: mithunroy@nitmanipur.ac.in, mithunroy.iisc@gmail.com

^b Department of Chemistry, Jadavpur University, Kolkata, West Bengal, India

^c Department of Chemistry, Vellore Institute of Technology, Vellore, Tamil Nadu, India

Abstract

We developed a novel Pd-catalysed enantioselective synthesis of C–N bonds using the chiral scaffold of DNA. The non-covalently linked [Pd(phen)(OAc)₂] with st-DNA catalysed the Markonicov hydroamination of β-nitrostyrene with methoxyamine for the first time with >75% enantiomeric excess (ee) in an aqueous buffer (pH 7.4) at room temperature.

This article is part of the themed collection: Catalysis & biocatalysis in OBC

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Article information

DOI: https://doi.org/10.1039/D1OB00714A
Article type: Communication
Submitted: 12 Apr 2021
Accepted: 10 May 2021
First published: 13 May 2021

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Org. Biomol. Chem., 2021,19, 5072-5076

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A noncovalent hybrid of [Pd(phen)(OAc)₂] and st-DNA for the enantioselective hydroamination of β-nitrostyrene with methoxyamine

M. Pal, D. Musib, M. Pal, G. Rana, G. Bag, S. Dutta and M. Roy, Org. Biomol. Chem., 2021, 19, 5072 DOI: 10.1039/D1OB00714A

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Organic & Biomolecular Chemistry