Journal of the Iranian Chemical Society, ( ISI ), Volume (13), No (6), Year (2016-6) , Pages (1105-1114)

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