Journal
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
Volume 13, Issue 6, Pages 1105-1114Publisher
SPRINGER
DOI: 10.1007/s13738-016-0824-z
Keywords
Kinetic controlled; syn-diastereoselective; Unfunctionalized ketones; Nano-Mn(HSO4)(2); Mannich reaction; Micelle
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Funding
- Ferdowsi University of Mashhad Research Council [3/23569]
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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. beta-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 beta-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.
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