Application of asymmetric Henry reaction by copper(II) complexes containing (R,R)-1,2-diaminocyclohexane with naphthyl and thiophenyl substituents

Juhyun Cho; Jong Hwa Jeong; Hyosun Lee; Jungkyu K. Lee; Saira Nayab

doi:10.1016/j.ica.2021.120492

Application of asymmetric Henry reaction by copper(II) complexes containing (R,R)-1,2-diaminocyclohexane with naphthyl and thiophenyl substituents

Juhyun Cho, Jong Hwa Jeong, Hyosun Lee, Jungkyu K. Lee, Saira Nayab

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

2 Scopus citations

Abstract

A series of Cu(II) complexes containing C₁-symmetric thiophene derivatives of (1R,2R)-N1-(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine, namely L¹, L² and L³ were synthesized and characterized. These complexes had distorted square-planar geometries around the Cu(II) center. High yield (99%) and excellent enantioselectivity (>99%) for (S)‐1‐nitro‐4‐phenylbutan‐2‐ol from the reaction of 3‐phenylpropanal and nitromethane was obtained using [L¹Cu(OAc)₂] or [L³Cu(OAc)₂] with 10 mol% of diisopropylethylamine (DIPEA) within 24 h. The catalytic systems also demonstrated good activity and moderate to high enantioselectivity for aliphatic aldehydes.

Original language	English
Article number	120492
Journal	Inorganica Chimica Acta
Volume	525
DOIs	https://doi.org/10.1016/j.ica.2021.120492
State	Published - 24 Sep 2021

Keywords

Asymmetric Henry reaction
Copper(II) complexes
Unsymmetrical chiral diamine ligands
β-Nitroalcohols

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title = "Application of asymmetric Henry reaction by copper(II) complexes containing (R,R)-1,2-diaminocyclohexane with naphthyl and thiophenyl substituents",

abstract = "A series of Cu(II) complexes containing C1-symmetric thiophene derivatives of (1R,2R)-N1-(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine, namely L1, L2 and L3 were synthesized and characterized. These complexes had distorted square-planar geometries around the Cu(II) center. High yield (99%) and excellent enantioselectivity (>99%) for (S)‐1‐nitro‐4‐phenylbutan‐2‐ol from the reaction of 3‐phenylpropanal and nitromethane was obtained using [L1Cu(OAc)2] or [L3Cu(OAc)2] with 10 mol% of diisopropylethylamine (DIPEA) within 24 h. The catalytic systems also demonstrated good activity and moderate to high enantioselectivity for aliphatic aldehydes.",

keywords = "Asymmetric Henry reaction, Copper(II) complexes, Unsymmetrical chiral diamine ligands, β-Nitroalcohols",

author = "Juhyun Cho and Jeong, {Jong Hwa} and Hyosun Lee and Lee, {Jungkyu K.} and Saira Nayab",

note = "Publisher Copyright: {\textcopyright} 2021 Elsevier B.V.",

year = "2021",

month = sep,

day = "24",

doi = "10.1016/j.ica.2021.120492",

language = "English",

volume = "525",

journal = "Inorganica Chimica Acta",

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T1 - Application of asymmetric Henry reaction by copper(II) complexes containing (R,R)-1,2-diaminocyclohexane with naphthyl and thiophenyl substituents

AU - Cho, Juhyun

AU - Jeong, Jong Hwa

AU - Lee, Hyosun

AU - Lee, Jungkyu K.

AU - Nayab, Saira

PY - 2021/9/24

Y1 - 2021/9/24

N2 - A series of Cu(II) complexes containing C1-symmetric thiophene derivatives of (1R,2R)-N1-(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine, namely L1, L2 and L3 were synthesized and characterized. These complexes had distorted square-planar geometries around the Cu(II) center. High yield (99%) and excellent enantioselectivity (>99%) for (S)‐1‐nitro‐4‐phenylbutan‐2‐ol from the reaction of 3‐phenylpropanal and nitromethane was obtained using [L1Cu(OAc)2] or [L3Cu(OAc)2] with 10 mol% of diisopropylethylamine (DIPEA) within 24 h. The catalytic systems also demonstrated good activity and moderate to high enantioselectivity for aliphatic aldehydes.

AB - A series of Cu(II) complexes containing C1-symmetric thiophene derivatives of (1R,2R)-N1-(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine, namely L1, L2 and L3 were synthesized and characterized. These complexes had distorted square-planar geometries around the Cu(II) center. High yield (99%) and excellent enantioselectivity (>99%) for (S)‐1‐nitro‐4‐phenylbutan‐2‐ol from the reaction of 3‐phenylpropanal and nitromethane was obtained using [L1Cu(OAc)2] or [L3Cu(OAc)2] with 10 mol% of diisopropylethylamine (DIPEA) within 24 h. The catalytic systems also demonstrated good activity and moderate to high enantioselectivity for aliphatic aldehydes.

KW - Asymmetric Henry reaction

KW - Copper(II) complexes

KW - Unsymmetrical chiral diamine ligands

KW - β-Nitroalcohols

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U2 - 10.1016/j.ica.2021.120492

DO - 10.1016/j.ica.2021.120492

M3 - Article

AN - SCOPUS:85107648897

SN - 0020-1693

VL - 525

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

M1 - 120492

ER -

Application of asymmetric Henry reaction by copper(II) complexes containing (R,R)-1,2-diaminocyclohexane with naphthyl and thiophenyl substituents

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Keywords

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