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- Title
Enantioselective Organocatalyzed Michael Addition of Isobutyraldehyde to Maleimides in Aqueous Media.
- Authors
Shim, Jae Ho; Cheun, Seok Hyun; Kim, Hyeon Soo; Ha, Deok-Chan
- 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.
- Subjects
ORGANIC reaction mechanisms; MICHAEL reaction; MALEIMIDES; HYDROGEN bonding; WATER use
- Publication
Molecules, 2022, Vol 27, Issue 9, p2759
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules27092759