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Enantioselective Organocatalyzed Michael Addition of Isobutyraldehyde to Maleimides in Aqueous Mediaopen access

Authors
Shim, Jae HoCheun, Seok HyunKim, Hyeon SooHa, Deok-Chan
Issue Date
5월-2022
Publisher
MDPI
Keywords
organocatalyst; enantioselectivity; Michael addition; aldehydes; succinimides; spironolactone
Citation
MOLECULES, v.27, no.9
Indexed
SCIE
SCOPUS
Journal Title
MOLECULES
Volume
27
Number
9
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/141767
DOI
10.3390/molecules27092759
ISSN
1420-3049
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.
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