Organocatalytic asymmetric michael addition of ketones to α, β-unsaturated nitro compounds

Jae Ho Shim; Si Hun Nam; Byeong Seon Kim; Deok Chan Ha

doi:10.3390/catal10060618

Organocatalytic asymmetric michael addition of ketones to α, β-unsaturated nitro compounds

Jae Ho Shim, Si Hun Nam, Byeong Seon Kim, Deok Chan Ha

College of Science

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

9 Citations (Scopus)

Abstract

An organic catalyst “(R, R)-1,2-diphenylethylenediamine(DPEN) derivative” was devel-oped as a chiral bifunctional organocatalyst and applied for asymmetric Michael additions of aromatic ketones to trans-β-nitroalkene compounds under neutral conditions. The isopropyl-subs-tituted thiourea catalyst in neutral condition provides high chemical yield and enantioselectivities (ee) (up to 96% yield, 98% ee).

Original language	English
Article number	618
Journal	Catalysts
Volume	10
Issue number	6
DOIs	https://doi.org/10.3390/catal10060618
Publication status	Published - 2020 Jun

Bibliographical note

Funding Information:
Funding: This work was support by National Research Foundation of Korea (NRF) grant funded by the Korean government [NRF-2019R1814112], [NRF-2020R1C1C1013785].

Publisher Copyright:
© 2020 by the authors. Licensee MDPI, Basel, Switzerland.

Keywords

Asymmetric
Enantioselectivity
Organocatalyst
Thiourea catalyst
Yield

ASJC Scopus subject areas

General Environmental Science
Catalysis
Physical and Theoretical Chemistry

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10.3390/catal10060618

Cite this

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title = "Organocatalytic asymmetric michael addition of ketones to α, β-unsaturated nitro compounds",

abstract = "An organic catalyst “(R, R)-1,2-diphenylethylenediamine(DPEN) derivative” was devel-oped as a chiral bifunctional organocatalyst and applied for asymmetric Michael additions of aromatic ketones to trans-β-nitroalkene compounds under neutral conditions. The isopropyl-subs-tituted thiourea catalyst in neutral condition provides high chemical yield and enantioselectivities (ee) (up to 96% yield, 98% ee).",

keywords = "Asymmetric, Enantioselectivity, Organocatalyst, Thiourea catalyst, Yield",

author = "Shim, {Jae Ho} and Nam, {Si Hun} and Kim, {Byeong Seon} and Ha, {Deok Chan}",

note = "Funding Information: Funding: This work was support by National Research Foundation of Korea (NRF) grant funded by the Korean government [NRF-2019R1814112], [NRF-2020R1C1C1013785]. Publisher Copyright: {\textcopyright} 2020 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2020",

month = jun,

doi = "10.3390/catal10060618",

language = "English",

volume = "10",

journal = "Catalysts",

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TY - JOUR

T1 - Organocatalytic asymmetric michael addition of ketones to α, β-unsaturated nitro compounds

AU - Shim, Jae Ho

AU - Nam, Si Hun

AU - Kim, Byeong Seon

AU - Ha, Deok Chan

N1 - Funding Information: Funding: This work was support by National Research Foundation of Korea (NRF) grant funded by the Korean government [NRF-2019R1814112], [NRF-2020R1C1C1013785]. Publisher Copyright: © 2020 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2020/6

Y1 - 2020/6

N2 - An organic catalyst “(R, R)-1,2-diphenylethylenediamine(DPEN) derivative” was devel-oped as a chiral bifunctional organocatalyst and applied for asymmetric Michael additions of aromatic ketones to trans-β-nitroalkene compounds under neutral conditions. The isopropyl-subs-tituted thiourea catalyst in neutral condition provides high chemical yield and enantioselectivities (ee) (up to 96% yield, 98% ee).

AB - An organic catalyst “(R, R)-1,2-diphenylethylenediamine(DPEN) derivative” was devel-oped as a chiral bifunctional organocatalyst and applied for asymmetric Michael additions of aromatic ketones to trans-β-nitroalkene compounds under neutral conditions. The isopropyl-subs-tituted thiourea catalyst in neutral condition provides high chemical yield and enantioselectivities (ee) (up to 96% yield, 98% ee).

KW - Asymmetric

KW - Enantioselectivity

KW - Organocatalyst

KW - Thiourea catalyst

KW - Yield

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U2 - 10.3390/catal10060618

DO - 10.3390/catal10060618

M3 - Article

AN - SCOPUS:85088802562

SN - 2073-4344

VL - 10

JO - Catalysts

JF - Catalysts

IS - 6

M1 - 618

ER -

Organocatalytic asymmetric michael addition of ketones to α, β-unsaturated nitro compounds

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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