Synthesis of β-Amino Ketones Using Titania Based on Solid Acid as A Catalyst

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Samet, Masoud | 2009

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Type of Document: M.Sc. Thesis
Language: Farsi
Document No: 39002 (03)
University: Sharif University of Technology
Department: Chemistry
Advisor(s): Mahmoudi Hashemi, Mohammad
Abstract:
Enanthioselective synthesis of biological molecules are so important in synthetic chemistry, and because of their biological activities, β-amino carbonyl compounds have earned so much attention in this area of chemistry. Mannich reaction is a classical method for synthesis of these molecules. The Mannich reaction is a three-component reaction between an enolizable CH-acidic carbonyl compound, an amine, and an aldehyde producing β-amino carbonyl compounds. But acidic or basic difficult circumstances, long reaction time, low yield and enantioselectivity, are the drawbacks of classical methods. In this project, we used titania-based solid acid as an enantioselective catalyst to overcome these problems. The catalyst bed was studied in two scales, nanometer and micrometer. The data clearly showed the reaction gave the corresponding β-amino ketones in good to high yield with good to excellent anti selectivity for cyclohexanone at room temperature. Interestingly, in the case of cycloheptanone the reaction showed reverse stereoselectivity and syn isomer was formed in high yield
Keywords:
Mannich Reaction ; Solid Acid Catalyst ; Titanium Dioxide ; B-Amino Ketones