Chemoselective Organocatalyzed Aldol Reactions

  • Chemoselectivity is the selectivity observed when a chemical reagent reacts preferentially with a particular functional group in a molecule having two or more different functional groups. The concept is routinely applied during complex syntheses to avoid the use of protecting groups. Thus, broadening chemoselectivity should lead to increased tactical or yield or waste reduction advantages during natural product or drug syntheses. With this in mind, I have investigated the reaction of aldehydes with cyclohexanones containing a 4-substituted linear or branched 1,3-diketone unit (triketones). The question was, could amino acid catalysis chemoselectively provide either the aldol or Knoevenagel condensation product? The key to this question was understanding the different mechanisms of these reactions and then exploiting those differences by tailoring the reaction medium to favor one over the other. A comprehensive experimental section detailing the synthesis of the aldol catalysts, synthesis of the triketone substrates, and formation of Knoevenagel and aldol products is additionally provided.

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Meta data
Publishing Institution:IRC-Library, Information Resource Center der Jacobs University Bremen
Granting Institution:Jacobs Univ.
Referee:Thomas Nugent, Nikolai Kuhnert, Vijay Wakchaure
Advisor:Thomas Nugent
Persistent Identifier (URN):urn:nbn:de:gbv:579-opus-1009662
Document Type:PhD Thesis
Date of Successful Oral Defense:2021/02/26
Date of First Publication:2021/05/05
Academic Department:Life Sciences & Chemistry
PhD Degree:Chemistry
Focus Area:Health
Other Countries Involved:United States of America
Call No:Diss 2021 / 2

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