Title : ( Effect of sodium dodecyl sulfate surfactant on regioselectivity and reversed diastereoselectivity of β-aminocarbonyl compounds in Mannich reaction )
Authors: Mahya Kohansal moghadam , Hossein Eshghi ,Access to full-text not allowed by authors
Abstract
Regioselective and diastereoselective synthesis of β-aminocarbonyl compounds is examined in the presence/absence of sodium dodecyl sulfate (SDS) as surfactant. Mannich reaction between derivatives of aniline, benzaldehyde and 2-butanone is performed in different conditions. The optimum condition are acquired include 1 mol % SDS per reactants in aqueous solvent at room temperature. Finding show conditions successfully employed to achieve remarkable kinetic control for the regioselective less-substituted Mannich product. In the absence of surfactant, other regioisomer; the more-substituted Mannich products (thermodynamic control) are obtained in slightly too moderate syn-diastereoselectivity depending on the substituent type on aniline. Although kinetic control produces less-substituted regioisomer but diasteroselectivity of the minor product is highly preferred anti-isomer which affected in the presence of surfactant.
Keywords
, Diastereoselective Regioselective β, aminocarbonyl Mannich reaction Sodium dodecyl sulfate@article{paperid:1097773,
author = {Kohansal Moghadam, Mahya and Eshghi, Hossein},
title = {Effect of sodium dodecyl sulfate surfactant on regioselectivity and reversed diastereoselectivity of β-aminocarbonyl compounds in Mannich reaction},
journal = {Journal of Molecular Liquids},
year = {2024},
volume = {398},
month = {February},
issn = {0167-7322},
pages = {124133--124139},
numpages = {6},
keywords = {Diastereoselective
Regioselective
β-aminocarbonyl
Mannich reaction
Sodium dodecyl sulfate},
}
%0 Journal Article
%T Effect of sodium dodecyl sulfate surfactant on regioselectivity and reversed diastereoselectivity of β-aminocarbonyl compounds in Mannich reaction
%A Kohansal Moghadam, Mahya
%A Eshghi, Hossein
%J Journal of Molecular Liquids
%@ 0167-7322
%D 2024