The Bull-James assembly: Efficient iminoboronate complex formation for chiral derivatization and supramolecular assembly

Robin R. Groleau; Tony D. James; Steven D. Bull

doi:10.1016/j.ccr.2020.213599

The Bull-James assembly: Efficient iminoboronate complex formation for chiral derivatization and supramolecular assembly

Robin R. Groleau, Tony D. James, Steven D. Bull

Department of Chemistry

Research output: Contribution to journal › Review article › peer-review

21 Citations (SciVal)

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Abstract

Chiral molecules are widely used in many fields of research and so practically simple, accurate methods to measure their enantiopurities are required. This review's initial focus is on one such method, the Bull-James assembly, which employs a three-component protocol combining 2-formylphenyl boronic acid, an amine, and a diol to self-assemble diastereomeric iminoboronate ester (IBE) complexes whose ratio can be used to measure the ee's of amine and diol analytes using ¹H and ¹⁹F NMR spectroscopic analysis. Examples where this supramolecular IBE assembly approach has been adapted to determine the ee of a range of analytes using other analytical techniques such as circular dichroism, fluorescence, and electrochemistry that are potentially applicable to high-throughput ee analysis are also discussed. Selected examples where this orthogonal self-assembly process has been used as a platform technology to construct boracyles, chiral auxiliaries/ligands, synthesise intelligent polymers/hydrogels, and prepare labelled peptides/proteins/biomolecules are also discussed.

Original language	English
Article number	213599
Journal	Coordination Chemistry Reviews
Volume	428
Early online date	20 Nov 2020
DOIs	https://doi.org/10.1016/j.ccr.2020.213599
Publication status	Published - 1 Feb 2021

Bibliographical note

Funding Information:
We would like to thank the many past members of the Bull and James groups who have contributed to the development of the Bull-James assembly (including Drs. Susumu Arimori, Andrew Kelly, Yolanda Perez-Fuertes, Sonia Lozano-Yeste, Magdalena Powell, Ewan Galbraith, David Tickell and Prof. John Fossey), as well as the many local and international collaborators who have also worked on this project. The contributions of the Material and Chemical Characterisation (MC2) facility at the University of Bath must also be acknowledged, with particular mention of our crystallographers Drs Gabriel Kociok-K?hn and Mary Mahon. We would like to thank the University of Bath, the Royal Society and EPSRC for their generous support over the past 20 years (EPSRC Grants: EP/D075351/1, GR/S70289/01). RRG would like to thank the EPSRC Centre for Doctoral Training in Catalysis for funding and support (EP/L016443/1). TDJ would like to thank the Royal Society for a Wolfson Research Merit Award. SDB would like to thank the Royal Society for an International Travel Award (IEC\R3|183068) that provided much needed time to write this review.

Funding Information:
We would like to thank the University of Bath , the Royal Society and EPSRC for their generous support over the past 20 years (EPSRC Grants: EP/D075351/1 , GR/S70289/01 ). RRG would like to thank the EPSRC Centre for Doctoral Training in Catalysis for funding and support ( EP/L016443/1 ). TDJ would like to thank the Royal Society for a Wolfson Research Merit Award. SDB would like to thank the Royal Society for an International Travel Award (IEC\R3|183068) that provided much needed time to write this review.

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.ccr.2020.213599

Bull-James Review_20122020Accepted author manuscript, 4.63 MBLicence: CC BY-NC-ND

Cite this

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title = "The Bull-James assembly: Efficient iminoboronate complex formation for chiral derivatization and supramolecular assembly",

abstract = "Chiral molecules are widely used in many fields of research and so practically simple, accurate methods to measure their enantiopurities are required. This review's initial focus is on one such method, the Bull-James assembly, which employs a three-component protocol combining 2-formylphenyl boronic acid, an amine, and a diol to self-assemble diastereomeric iminoboronate ester (IBE) complexes whose ratio can be used to measure the ee's of amine and diol analytes using 1H and 19F NMR spectroscopic analysis. Examples where this supramolecular IBE assembly approach has been adapted to determine the ee of a range of analytes using other analytical techniques such as circular dichroism, fluorescence, and electrochemistry that are potentially applicable to high-throughput ee analysis are also discussed. Selected examples where this orthogonal self-assembly process has been used as a platform technology to construct boracyles, chiral auxiliaries/ligands, synthesise intelligent polymers/hydrogels, and prepare labelled peptides/proteins/biomolecules are also discussed.",

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note = "Funding Information: We would like to thank the many past members of the Bull and James groups who have contributed to the development of the Bull-James assembly (including Drs. Susumu Arimori, Andrew Kelly, Yolanda Perez-Fuertes, Sonia Lozano-Yeste, Magdalena Powell, Ewan Galbraith, David Tickell and Prof. John Fossey), as well as the many local and international collaborators who have also worked on this project. The contributions of the Material and Chemical Characterisation (MC2) facility at the University of Bath must also be acknowledged, with particular mention of our crystallographers Drs Gabriel Kociok-K?hn and Mary Mahon. We would like to thank the University of Bath, the Royal Society and EPSRC for their generous support over the past 20 years (EPSRC Grants: EP/D075351/1, GR/S70289/01). RRG would like to thank the EPSRC Centre for Doctoral Training in Catalysis for funding and support (EP/L016443/1). TDJ would like to thank the Royal Society for a Wolfson Research Merit Award. SDB would like to thank the Royal Society for an International Travel Award (IEC\R3|183068) that provided much needed time to write this review. Funding Information: We would like to thank the University of Bath , the Royal Society and EPSRC for their generous support over the past 20 years (EPSRC Grants: EP/D075351/1 , GR/S70289/01 ). RRG would like to thank the EPSRC Centre for Doctoral Training in Catalysis for funding and support ( EP/L016443/1 ). TDJ would like to thank the Royal Society for a Wolfson Research Merit Award. SDB would like to thank the Royal Society for an International Travel Award (IEC\R3|183068) that provided much needed time to write this review. ",

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The Bull-James assembly: Efficient iminoboronate complex formation for chiral derivatization and supramolecular assembly

Abstract

Bibliographical note

ASJC Scopus subject areas

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HIGH RESOLUTION MASS SPECTROMETERS TO SUPPORT CHEMISTRY AT B ATH

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The Bull-James assembly: Efficient iminoboronate complex formation for chiral derivatization and supramolecular assembly

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

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HIGH RESOLUTION MASS SPECTROMETERS TO SUPPORT CHEMISTRY AT B ATH

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