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

^*Corresponding author for this work

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

9 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",

language = "English",

volume = "10",

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journal = "RSC Advances",

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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.

UR - https://www.scopus.com/pages/publications/85090923282

U2 - 10.1039/d0ra03550e

DO - 10.1039/d0ra03550e

M3 - Article

AN - SCOPUS:85090923282

SN - 2046-2069

VL - 10

SP - 31808

EP - 31814

JO - RSC Advances

JF - RSC Advances

IS - 53

ER -

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

Abstract

Bibliographical note

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