Mind the gap! Steric-driven reductive desymmetrisation of malononitriles

Cara Philipson; Reece H. Hoogesteger; Craig P. Johnston

doi:10.1016/j.trechm.2024.12.002

Mind the gap! Steric-driven reductive desymmetrisation of malononitriles

Cara Philipson, Reece H. Hoogesteger, Craig P. Johnston^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Huang and coworkers recently demonstrated that a cobalt(I)-hydride complex, ligated with a finely tuned chiral bisoxazoline ligand, can selectively reduce disubstituted malononitriles by discriminating between enantiotopic nitrile groups. This reductive desymmetrisation strategy utilises the bulk industrial feedstock malononitrile to access nitrogen-rich enantioenriched products.

Original language	English
Pages (from-to)	59-61
Number of pages	3
Journal	Trends in Chemistry
Volume	7
Issue number	2
Early online date	12 Feb 2025
DOIs	https://doi.org/10.1016/j.trechm.2024.12.002
Publication status	Published - 12 Feb 2025

Keywords

Enantioselective
Desymmetrisation
Cobalt
Reduction
Malononitrile

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10.1016/j.trechm.2024.12.002Licence: CC BY

Philipson_2025_TiC_Mind-the-gap-desymmetrisation-malononitriles_CC
© 2024 The Author(s). This is an open access article under the CC BY license (https://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Final published version, 731 KBLicence: CC BY

2 Finished
2 Active

Craig Johnston URF: Enantioseletive Catalysis with Carbocation Surrogates
Johnston, C. P. (PI)
The Royal Society
1/10/23 → 30/09/26
Project: Fellowship
Catalytic Hydrofluorination: Catalytic Hydrofluorination for the Assembly of Chiral Fluorinated Building Blocks
Johnston, C. P. (PI)
EPSRC
1/04/23 → 31/03/26
Project: Standard
RS URF 2018 Craig Johnston: Enantioselective radical reactions facilitated by ion-bindong catalysis
Johnston, C. P. (PI)
1/10/18 → 30/09/23
Project: Fellowship

Cite this

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title = "Mind the gap! Steric-driven reductive desymmetrisation of malononitriles",

abstract = "Huang and coworkers recently demonstrated that a cobalt(I)-hydride complex, ligated with a finely tuned chiral bisoxazoline ligand, can selectively reduce disubstituted malononitriles by discriminating between enantiotopic nitrile groups. This reductive desymmetrisation strategy utilises the bulk industrial feedstock malononitrile to access nitrogen-rich enantioenriched products.",

keywords = "Enantioselective, Desymmetrisation, Cobalt, Reduction, Malononitrile",

author = "Cara Philipson and Hoogesteger, {Reece H.} and Johnston, {Craig P.}",

note = "Funding: The authors acknowledge financial support from Syngenta, EPSRC (EP/X013081/1) and The Royal Society (University Research Fellowship URF\R1\180017, URF\R\231016, and associated Enhancement Award RGF\EA\181022).",

year = "2025",

month = feb,

day = "12",

doi = "10.1016/j.trechm.2024.12.002",

language = "English",

volume = "7",

pages = "59--61",

journal = "Trends in Chemistry",

issn = "2589-7209",

publisher = "Elsevier Inc.",

number = "2",

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TY - JOUR

T1 - Mind the gap! Steric-driven reductive desymmetrisation of malononitriles

AU - Philipson, Cara

AU - Hoogesteger, Reece H.

AU - Johnston, Craig P.

N1 - Funding: The authors acknowledge financial support from Syngenta, EPSRC (EP/X013081/1) and The Royal Society (University Research Fellowship URF\R1\180017, URF\R\231016, and associated Enhancement Award RGF\EA\181022).

PY - 2025/2/12

Y1 - 2025/2/12

N2 - Huang and coworkers recently demonstrated that a cobalt(I)-hydride complex, ligated with a finely tuned chiral bisoxazoline ligand, can selectively reduce disubstituted malononitriles by discriminating between enantiotopic nitrile groups. This reductive desymmetrisation strategy utilises the bulk industrial feedstock malononitrile to access nitrogen-rich enantioenriched products.

AB - Huang and coworkers recently demonstrated that a cobalt(I)-hydride complex, ligated with a finely tuned chiral bisoxazoline ligand, can selectively reduce disubstituted malononitriles by discriminating between enantiotopic nitrile groups. This reductive desymmetrisation strategy utilises the bulk industrial feedstock malononitrile to access nitrogen-rich enantioenriched products.

KW - Enantioselective

KW - Desymmetrisation

KW - Cobalt

KW - Reduction

KW - Malononitrile

U2 - 10.1016/j.trechm.2024.12.002

DO - 10.1016/j.trechm.2024.12.002

M3 - Article

SN - 2589-7209

VL - 7

SP - 59

EP - 61

JO - Trends in Chemistry

JF - Trends in Chemistry

IS - 2

ER -

Mind the gap! Steric-driven reductive desymmetrisation of malononitriles

Abstract

Keywords

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Projects

Craig Johnston URF: Enantioseletive Catalysis with Carbocation Surrogates

Catalytic Hydrofluorination: Catalytic Hydrofluorination for the Assembly of Chiral Fluorinated Building Blocks

RS URF 2018 Craig Johnston: Enantioselective radical reactions facilitated by ion-bindong catalysis

Cite this