Enantioselective Organocatalyzed Michael Addition of Isobutyraldehyde to Maleimides in Aqueous Media
DC Field | Value | Language |
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dc.contributor.author | Shim, Jae Ho | - |
dc.contributor.author | Cheun, Seok Hyun | - |
dc.contributor.author | Kim, Hyeon Soo | - |
dc.contributor.author | Ha, Deok-Chan | - |
dc.date.accessioned | 2022-06-09T19:40:43Z | - |
dc.date.available | 2022-06-09T19:40:43Z | - |
dc.date.created | 2022-06-09 | - |
dc.date.issued | 2022-05 | - |
dc.identifier.issn | 1420-3049 | - |
dc.identifier.uri | https://scholar.korea.ac.kr/handle/2021.sw.korea/141767 | - |
dc.description.abstract | Thiourea was introduced into (R,R)-1,2-diphenylethylenediamine as an organocatalyst to promote the reaction between isobutyraldehydes and maleimides. Enantioselective Michael addition reaction was carried out as an eco-friendly method using water as the solvent. As a result of the reaction between isobutyraldehyde and maleimide, >= 97% yield and 99% enantioselectivity were obtained at a low catalyst loading of 0.01 mol%. The solvent effect can be explained by theoretical calculations that indicate the participation of a transition state, in which the CF3 substituent of the catalyst is a hydrogen bond activated by the surrounding water molecules. This discovery enabled the use of low catalyst loading in the organic reactions of chiral substances for pharmaceutical applications. Furthermore, a solvent effect for Michael reaction of the organocatalysts was proposed, and the organic reaction mechanisms were determined through quantum calculations. | - |
dc.language | English | - |
dc.language.iso | en | - |
dc.publisher | MDPI | - |
dc.subject | ALPHA,ALPHA-DISUBSTITUTED ALDEHYDES | - |
dc.subject | CONJUGATE ADDITION | - |
dc.subject | AMINO | - |
dc.title | Enantioselective Organocatalyzed Michael Addition of Isobutyraldehyde to Maleimides in Aqueous Media | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Shim, Jae Ho | - |
dc.identifier.doi | 10.3390/molecules27092759 | - |
dc.identifier.scopusid | 2-s2.0-85129033657 | - |
dc.identifier.wosid | 000799227600001 | - |
dc.identifier.bibliographicCitation | MOLECULES, v.27, no.9 | - |
dc.relation.isPartOf | MOLECULES | - |
dc.citation.title | MOLECULES | - |
dc.citation.volume | 27 | - |
dc.citation.number | 9 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.isOpenAccess | Y | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Biochemistry & Molecular Biology | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Biochemistry & Molecular Biology | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Multidisciplinary | - |
dc.subject.keywordPlus | ALPHA,ALPHA-DISUBSTITUTED ALDEHYDES | - |
dc.subject.keywordPlus | CONJUGATE ADDITION | - |
dc.subject.keywordPlus | AMINO | - |
dc.subject.keywordAuthor | organocatalyst | - |
dc.subject.keywordAuthor | enantioselectivity | - |
dc.subject.keywordAuthor | Michael addition | - |
dc.subject.keywordAuthor | aldehydes | - |
dc.subject.keywordAuthor | succinimides | - |
dc.subject.keywordAuthor | spironolactone | - |
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