Planar chiral pseudo-isocoumarins by copper catalysed desymmetrisation

Adam J. Wright; Fiona J. McMartin; Liam G. Dyer; Lloyd H. Sayer; Philip C. Bulman Page; G. Richard Stephenson

doi:10.1002/ejic.202100841

Planar chiral pseudo-isocoumarins by copper catalysed desymmetrisation

Adam J. Wright, Fiona J. McMartin, Liam G. Dyer, Lloyd H. Sayer, Philip C. Bulman Page, G. Richard Stephenson

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

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Abstract

A new copper catalysed desymmetrisation reaction of bisalkynyl ferrocenecarboxylic acids results in the first asymmetric synthesis of planar chiral pseudo-isocoumarins in up to 64 % enantiomeric excess and up to 99 % yield. The absolute configuration of the chiral heterocycles is proven by chemical correlation and circular dichroism spectroscopy, opening the way for the rational extension of this method to produce bioactive isocoumarin-fused ferrocene derivatives.

Original language	English
Article number	e202100841
Journal	European Journal of Inorganic Chemistry
Volume	2022
Issue number	12
Early online date	7 Apr 2022
DOIs	https://doi.org/10.1002/ejic.202100841
Publication status	Published - 27 Apr 2022

Keywords

Asymmetric catalysis
Asymmetric synthesis
Chirality
Circular dichroism
Metallocenes

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10.1002/ejic.202100841Licence: CC BY-NC-ND

Euro J of Inorganic Chem - 2022 - Wright - Planar Chiral Pseudo‐Isocoumarins by Copper Catalysed DesymmetrisationFinal published version, 1.15 MBLicence: CC BY-NC-ND

https://onlinelibrary.wiley.com/doi/10.1002/ejic.202100841Licence: CC BY-NC-ND

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title = "Planar chiral pseudo-isocoumarins by copper catalysed desymmetrisation",

abstract = "A new copper catalysed desymmetrisation reaction of bisalkynyl ferrocenecarboxylic acids results in the first asymmetric synthesis of planar chiral pseudo-isocoumarins in up to 64 % enantiomeric excess and up to 99 % yield. The absolute configuration of the chiral heterocycles is proven by chemical correlation and circular dichroism spectroscopy, opening the way for the rational extension of this method to produce bioactive isocoumarin-fused ferrocene derivatives.",

keywords = "Asymmetric catalysis, Asymmetric synthesis, Chirality, Circular dichroism, Metallocenes",

author = "Wright, {Adam J.} and McMartin, {Fiona J.} and Dyer, {Liam G.} and Sayer, {Lloyd H.} and {Bulman Page}, {Philip C.} and Stephenson, {G. Richard}",

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T1 - Planar chiral pseudo-isocoumarins by copper catalysed desymmetrisation

AU - Wright, Adam J.

AU - McMartin, Fiona J.

AU - Dyer, Liam G.

AU - Sayer, Lloyd H.

AU - Bulman Page, Philip C.

AU - Stephenson, G. Richard

PY - 2022/4/27

Y1 - 2022/4/27

N2 - A new copper catalysed desymmetrisation reaction of bisalkynyl ferrocenecarboxylic acids results in the first asymmetric synthesis of planar chiral pseudo-isocoumarins in up to 64 % enantiomeric excess and up to 99 % yield. The absolute configuration of the chiral heterocycles is proven by chemical correlation and circular dichroism spectroscopy, opening the way for the rational extension of this method to produce bioactive isocoumarin-fused ferrocene derivatives.

AB - A new copper catalysed desymmetrisation reaction of bisalkynyl ferrocenecarboxylic acids results in the first asymmetric synthesis of planar chiral pseudo-isocoumarins in up to 64 % enantiomeric excess and up to 99 % yield. The absolute configuration of the chiral heterocycles is proven by chemical correlation and circular dichroism spectroscopy, opening the way for the rational extension of this method to produce bioactive isocoumarin-fused ferrocene derivatives.

KW - Asymmetric catalysis

KW - Asymmetric synthesis

KW - Chirality

KW - Circular dichroism

KW - Metallocenes

UR - http://www.scopus.com/inward/record.url?scp=85127572012&partnerID=8YFLogxK

U2 - 10.1002/ejic.202100841

DO - 10.1002/ejic.202100841

M3 - Article

SN - 1434-1948

VL - 2022

JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

IS - 12

M1 - e202100841

ER -

Planar chiral pseudo-isocoumarins by copper catalysed desymmetrisation

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Keywords

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