Characterization of stereoisomeric 5-(2-nitro-1-phenylethyl)furan-2(5H)-ones by computation of 1H and 13C NMR chemical shifts and electronic circular dichroism spectra

Dayane T. Lopes; Thomas R. Hoye; Elson S. Alvarenga

doi:10.1002/mrc.5073

Characterization of stereoisomeric 5-(2-nitro-1-phenylethyl)furan-2(5H)-ones by computation of ¹H and ¹³C NMR chemical shifts and electronic circular dichroism spectra

Dayane T. Lopes, Thomas R. Hoye, Elson S. Alvarenga

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

4 Scopus citations

Abstract

In the present work, we describe the preparation of two diastereomers from the enantioselective Michael addition of furan-2(5H)-one to (E)-(2-nitrovinyl)benzene catalyzed by a dinuclear Zn-complex. The relative configurations of the diastereomeric products were assigned by comparing nuclear magnetic resonance (NMR) experimental chemical shift data with those computed by density functional theory (DFT) methods. Corrected mean absolute error (CMAE) and CP3 analyses were used to compare the data sets. The absolute configuration of each diastereomer was initially assigned by analysis of electronic circular dichroism (ECD) data, which was consistent with that of the known X-ray crystallographic structure of the product of a related reaction, namely, (R)-5-((R)-1-(4-chlorophenyl)-2-nitroethyl)furan-2(5H)-one.

Original language	English (US)
Pages (from-to)	43-51
Number of pages	9
Journal	Magnetic Resonance in Chemistry
Volume	59
Issue number	1
DOIs	https://doi.org/10.1002/mrc.5073
State	Published - Jul 15 2020

Bibliographical note

Funding Information:
We are grateful to Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), Fundação do Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG), RQ-MG (Rede Mineira de Química), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)—Finance Code 001, and the National Institute of General Medical Sciences of the U.S. Department of Health and Human Services (R35 GM127097) for financial support. Thanks to Victor Rubim Otati for recording the electronic CD spectra. This work was carried out in part using software and hardware resources made available through the University of Minnesota, Supercomputing Institute (MSI).

Funding Information:
We are grateful to Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), Fundação do Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG), RQ‐MG (Rede Mineira de Química), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)—Finance Code 001, and the National Institute of General Medical Sciences of the U.S. Department of Health and Human Services (R35 GM127097) for financial support. Thanks to Victor Rubim Otati for recording the electronic CD spectra. This work was carried out in part using software and hardware resources made available through the University of Minnesota, Supercomputing Institute (MSI).

Publisher Copyright:
© 2020 John Wiley & Sons, Ltd.

Keywords

CP3
DFT
ECD
MAE
Michael addition
NMR

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10.1002/mrc.5073

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@article{b172b1728f594b1c895420e0a4419181,

title = "Characterization of stereoisomeric 5-(2-nitro-1-phenylethyl)furan-2(5H)-ones by computation of 1H and 13C NMR chemical shifts and electronic circular dichroism spectra",

abstract = "In the present work, we describe the preparation of two diastereomers from the enantioselective Michael addition of furan-2(5H)-one to (E)-(2-nitrovinyl)benzene catalyzed by a dinuclear Zn-complex. The relative configurations of the diastereomeric products were assigned by comparing nuclear magnetic resonance (NMR) experimental chemical shift data with those computed by density functional theory (DFT) methods. Corrected mean absolute error (CMAE) and CP3 analyses were used to compare the data sets. The absolute configuration of each diastereomer was initially assigned by analysis of electronic circular dichroism (ECD) data, which was consistent with that of the known X-ray crystallographic structure of the product of a related reaction, namely, (R)-5-((R)-1-(4-chlorophenyl)-2-nitroethyl)furan-2(5H)-one.",

keywords = "CP3, DFT, ECD, MAE, Michael addition, NMR",

author = "Lopes, {Dayane T.} and Hoye, {Thomas R.} and Alvarenga, {Elson S.}",

note = "Funding Information: We are grateful to Conselho Nacional de Desenvolvimento Cient{\'i}fico e Tecnol{\'o}gico (CNPq), Funda{\c c}{\~a}o do Amparo {\`a} Pesquisa do Estado de Minas Gerais (FAPEMIG), RQ-MG (Rede Mineira de Qu{\'i}mica), Coordena{\c c}{\~a}o de Aperfei{\c c}oamento de Pessoal de N{\'i}vel Superior (CAPES)—Finance Code 001, and the National Institute of General Medical Sciences of the U.S. Department of Health and Human Services (R35 GM127097) for financial support. Thanks to Victor Rubim Otati for recording the electronic CD spectra. This work was carried out in part using software and hardware resources made available through the University of Minnesota, Supercomputing Institute (MSI). Funding Information: We are grateful to Conselho Nacional de Desenvolvimento Cient{\'i}fico e Tecnol{\'o}gico (CNPq), Funda{\c c}{\~a}o do Amparo {\`a} Pesquisa do Estado de Minas Gerais (FAPEMIG), RQ‐MG (Rede Mineira de Qu{\'i}mica), Coordena{\c c}{\~a}o de Aperfei{\c c}oamento de Pessoal de N{\'i}vel Superior (CAPES)—Finance Code 001, and the National Institute of General Medical Sciences of the U.S. Department of Health and Human Services (R35 GM127097) for financial support. Thanks to Victor Rubim Otati for recording the electronic CD spectra. This work was carried out in part using software and hardware resources made available through the University of Minnesota, Supercomputing Institute (MSI). Publisher Copyright: {\textcopyright} 2020 John Wiley & Sons, Ltd.",

year = "2020",

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doi = "10.1002/mrc.5073",

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T1 - Characterization of stereoisomeric 5-(2-nitro-1-phenylethyl)furan-2(5H)-ones by computation of 1H and 13C NMR chemical shifts and electronic circular dichroism spectra

AU - Lopes, Dayane T.

AU - Hoye, Thomas R.

AU - Alvarenga, Elson S.

N1 - Funding Information: We are grateful to Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), Fundação do Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG), RQ-MG (Rede Mineira de Química), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)—Finance Code 001, and the National Institute of General Medical Sciences of the U.S. Department of Health and Human Services (R35 GM127097) for financial support. Thanks to Victor Rubim Otati for recording the electronic CD spectra. This work was carried out in part using software and hardware resources made available through the University of Minnesota, Supercomputing Institute (MSI). Funding Information: We are grateful to Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), Fundação do Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG), RQ‐MG (Rede Mineira de Química), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)—Finance Code 001, and the National Institute of General Medical Sciences of the U.S. Department of Health and Human Services (R35 GM127097) for financial support. Thanks to Victor Rubim Otati for recording the electronic CD spectra. This work was carried out in part using software and hardware resources made available through the University of Minnesota, Supercomputing Institute (MSI). Publisher Copyright: © 2020 John Wiley & Sons, Ltd.

PY - 2020/7/15

Y1 - 2020/7/15

N2 - In the present work, we describe the preparation of two diastereomers from the enantioselective Michael addition of furan-2(5H)-one to (E)-(2-nitrovinyl)benzene catalyzed by a dinuclear Zn-complex. The relative configurations of the diastereomeric products were assigned by comparing nuclear magnetic resonance (NMR) experimental chemical shift data with those computed by density functional theory (DFT) methods. Corrected mean absolute error (CMAE) and CP3 analyses were used to compare the data sets. The absolute configuration of each diastereomer was initially assigned by analysis of electronic circular dichroism (ECD) data, which was consistent with that of the known X-ray crystallographic structure of the product of a related reaction, namely, (R)-5-((R)-1-(4-chlorophenyl)-2-nitroethyl)furan-2(5H)-one.

AB - In the present work, we describe the preparation of two diastereomers from the enantioselective Michael addition of furan-2(5H)-one to (E)-(2-nitrovinyl)benzene catalyzed by a dinuclear Zn-complex. The relative configurations of the diastereomeric products were assigned by comparing nuclear magnetic resonance (NMR) experimental chemical shift data with those computed by density functional theory (DFT) methods. Corrected mean absolute error (CMAE) and CP3 analyses were used to compare the data sets. The absolute configuration of each diastereomer was initially assigned by analysis of electronic circular dichroism (ECD) data, which was consistent with that of the known X-ray crystallographic structure of the product of a related reaction, namely, (R)-5-((R)-1-(4-chlorophenyl)-2-nitroethyl)furan-2(5H)-one.

KW - CP3

KW - DFT

KW - ECD

KW - MAE

KW - Michael addition

KW - NMR

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DO - 10.1002/mrc.5073

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SN - 0749-1581

VL - 59

SP - 43

EP - 51

JO - Magnetic Resonance in Chemistry

JF - Magnetic Resonance in Chemistry

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