Enantioselective organocatalytic Michael reactions using chiral (R,R)-1,2-diphenylethylenediamine-derived thioureas

Jae Ho Shim; Min Ji Lee; Min Ho Lee; Byeong Seon Kim; Deok Chan Ha

doi:10.1039/d0ra03550e

Enantioselective organocatalytic Michael reactions using chiral (R,R)-1,2-diphenylethylenediamine-derived thioureas

Jae Ho Shim, Min Ji Lee, Min Ho Lee, Byeong Seon Kim, Deok Chan Ha

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

8 Citations (Scopus)

Abstract

Although the Michael addition is a very well-known and widely applied reaction, cost-effective, metal-free, and readily prepared organic catalysts remain rare. A chiral, bifunctional, (R,R)-1,2-diphenylethylenediamine-derived thiourea organic catalyst was developed and applied to asymmetric Michael additions of nitroalkenes under neutral conditions. Generally, fluorine-substituted thiourea catalysts exhibited high chemical yields and enantioselectivities under neutral conditions. The mild reactions were tolerant of many functional groups and afforded good-to-excellent yields, as well as high diastereo- and enantioselectivities for the Michael adducts. The utility of the transformation was demonstrated by the synthesis of a bioactive compound, (R)-Phenibut.

Original language	English
Pages (from-to)	31808-31814
Number of pages	7
Journal	RSC Advances
Volume	10
Issue number	53
DOIs	https://doi.org/10.1039/d0ra03550e
Publication status	Published - 2020 Aug 27

Bibliographical note

Funding Information:
We are grateful for nancial support by Dr K. H. Kim. We gratefully acknowledge the support from National Research Foundation of Korea (NRF-2019R1814112), (NRF-2020R1C1C1-013785). We thank Dr Yeonsun Hong for providing assistance.

Publisher Copyright:
© The Royal Society of Chemistry 2020.

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering

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title = "Enantioselective organocatalytic Michael reactions using chiral (R,R)-1,2-diphenylethylenediamine-derived thioureas",

abstract = "Although the Michael addition is a very well-known and widely applied reaction, cost-effective, metal-free, and readily prepared organic catalysts remain rare. A chiral, bifunctional, (R,R)-1,2-diphenylethylenediamine-derived thiourea organic catalyst was developed and applied to asymmetric Michael additions of nitroalkenes under neutral conditions. Generally, fluorine-substituted thiourea catalysts exhibited high chemical yields and enantioselectivities under neutral conditions. The mild reactions were tolerant of many functional groups and afforded good-to-excellent yields, as well as high diastereo- and enantioselectivities for the Michael adducts. The utility of the transformation was demonstrated by the synthesis of a bioactive compound, (R)-Phenibut.",

author = "Shim, {Jae Ho} and Lee, {Min Ji} and Lee, {Min Ho} and Kim, {Byeong Seon} and Ha, {Deok Chan}",

note = "Funding Information: We are grateful for nancial support by Dr K. H. Kim. We gratefully acknowledge the support from National Research Foundation of Korea (NRF-2019R1814112), (NRF-2020R1C1C1-013785). We thank Dr Yeonsun Hong for providing assistance. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2020.",

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doi = "10.1039/d0ra03550e",

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T1 - Enantioselective organocatalytic Michael reactions using chiral (R,R)-1,2-diphenylethylenediamine-derived thioureas

AU - Shim, Jae Ho

AU - Lee, Min Ji

AU - Lee, Min Ho

AU - Kim, Byeong Seon

AU - Ha, Deok Chan

N1 - Funding Information: We are grateful for nancial support by Dr K. H. Kim. We gratefully acknowledge the support from National Research Foundation of Korea (NRF-2019R1814112), (NRF-2020R1C1C1-013785). We thank Dr Yeonsun Hong for providing assistance. Publisher Copyright: © The Royal Society of Chemistry 2020.

PY - 2020/8/27

Y1 - 2020/8/27

N2 - Although the Michael addition is a very well-known and widely applied reaction, cost-effective, metal-free, and readily prepared organic catalysts remain rare. A chiral, bifunctional, (R,R)-1,2-diphenylethylenediamine-derived thiourea organic catalyst was developed and applied to asymmetric Michael additions of nitroalkenes under neutral conditions. Generally, fluorine-substituted thiourea catalysts exhibited high chemical yields and enantioselectivities under neutral conditions. The mild reactions were tolerant of many functional groups and afforded good-to-excellent yields, as well as high diastereo- and enantioselectivities for the Michael adducts. The utility of the transformation was demonstrated by the synthesis of a bioactive compound, (R)-Phenibut.

AB - Although the Michael addition is a very well-known and widely applied reaction, cost-effective, metal-free, and readily prepared organic catalysts remain rare. A chiral, bifunctional, (R,R)-1,2-diphenylethylenediamine-derived thiourea organic catalyst was developed and applied to asymmetric Michael additions of nitroalkenes under neutral conditions. Generally, fluorine-substituted thiourea catalysts exhibited high chemical yields and enantioselectivities under neutral conditions. The mild reactions were tolerant of many functional groups and afforded good-to-excellent yields, as well as high diastereo- and enantioselectivities for the Michael adducts. The utility of the transformation was demonstrated by the synthesis of a bioactive compound, (R)-Phenibut.

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DO - 10.1039/d0ra03550e

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JO - RSC Advances

JF - RSC Advances

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ER -

Enantioselective organocatalytic Michael reactions using chiral (R,R)-1,2-diphenylethylenediamine-derived thioureas

Abstract

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