Title : ( One‑ pot three‑component kinetic controlled and syn‑ diastereoselective Mannich reaction of unfunctionalized ketones in water catalyzed by nano‑manganese hydrogen sulfate particles )
Authors: malihe hojjatirad , Hossein Eshghi , Seyed Mohammad Seyedi , Mohammad Rahimizadeh , fatemeh eshkil , Kamran Lamei ,
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Abstract
Direct catalytic three component Mannich reaction of aliphatic ketone, aldehyde and amine was described in the presence of a catalytic amount of nano-Mn(HSO4)2 (10 mol%) and a surfactant, for example sodium dodecyl sulfate (10 mol%) in the water as a green solvent. β-amino carbonyl compounds were obtained regioselectively as a less-substituted product from a one-pot three component Mannich reaction of 2-butanone in the above conditions. On the other hand, 3-pentanone as a symmetric ketone in the Mannich reactions gave β-amino carbonyl compounds with moderate to high syn diasterioselectivity. Control of regioselectivity and/or diasterioselectivity of the most products is related to micelle formation of organic substrates and SDS in water. Hydrophobic groups of substrates self-assembled in these microreactors whereas, hydrophilic groups were solvated with water or chelated with Mn(HSO4). The above interactions forwarded to these observed selectivity.
Keywords
, Kinetic controlled, syn-diastereoselective , Unfunctionalized ketones, Nano-Mn(HSO4)2, Mannich reaction, Micelle
@article{paperid:1054997,
author = {Hojjatirad, Malihe and Eshghi, Hossein and Seyedi, Seyed Mohammad and Rahimizadeh, Mohammad and Eshkil, Fatemeh and Lamei, Kamran},
title = {One‑ pot three‑component kinetic controlled and syn‑ diastereoselective Mannich reaction of unfunctionalized ketones in water catalyzed by nano‑manganese hydrogen sulfate particles},
journal = {Journal of the Iranian Chemical Society},
year = {2016},
volume = {13},
number = {6},
month = {June},
issn = {1735-207X},
pages = {1105--1114},
numpages = {9},
keywords = {Kinetic controlled; syn-diastereoselective ; Unfunctionalized ketones; Nano-Mn(HSO4)2; Mannich reaction; Micelle},
}
%0 Journal Article
%T One‑ pot three‑component kinetic controlled and syn‑ diastereoselective Mannich reaction of unfunctionalized ketones in water catalyzed by nano‑manganese hydrogen sulfate particles
%A Hojjatirad, Malihe
%A Eshghi, Hossein
%A Seyedi, Seyed Mohammad
%A Rahimizadeh, Mohammad
%A Eshkil, Fatemeh
%A Lamei, Kamran
%J Journal of the Iranian Chemical Society
%@ 1735-207X
%D 2016
