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Maria Candeia Kuliakita Sakukuma, Speaker at Catalysis Conferences
Federal University of Bahia, Angola
Title : Use of organocatalysis for the synthesis of phenyl-hydroxylated-butyric acids


Organocatalytic reactions are becoming powerful tools in the construction of complex molecular skeletons. In 2021, Benjamim List and David MacMillan were awarded the Nobel Prize in Chemistry for the development of asymmetric organocatalysis. In this work we used the organocatalysis reaction as key step to get the 4-(p-nitro)-phenylhydroxylated- butyric acids. The acids 1 (2,3-anti-3,4-syn) and 2 (2,3-syn-3,4-syn) were synthesized from TBSdihydroxyacetone (TBS-DHA) 3 and p-nitrobenzaldehyde 4 using an organocatalyzed aldol reaction as the key step. The stereoselectivity of the syn-aldol coupling was suggested as resulting from a transition state including a low energy anti-Z enamine, derived from the condensation of TBS-DHA and O-tBu-L-threonine. Selective anti- and syncarbonyl reduction of the carbonyl adducts led to 2,3-anti-3,4-syn and 2,3-syn-3,4-syn hydroxy compounds, respectively, which underwent the same sequence of transformations (ketal synthesis, primary TBS-deprotection, oxidation and deprotection) to afford 4-(p-nitro)-phenyl-hydroxylated-butyric acids 1 and 2 in seven steps and 22% and 24% overall yield, respectively.

Audience Takeaway Notes:

  • The public will be able to learn the experimental part, which is one of the main challenges of this work;
  • With this investigation in a similar way we will be able to prepare new chemical compounds;
  • The methodology used allows its extension to the teaching component;
  • Organocatalysis has numerous advantages.


Dr. Maria Candeia Kuliakita Sakukuma studied Chemistry at the Higher Institute of Education Sciences, Department of Exact Sciences, 230, Isced-Huíla, Lubango, Angola and graduated. She then joined the research group of Prof. Maurício Victor at Chemistry Institute, Federal University of Bahia, UFBA, in 2014, when received her MS and PhD degree in 2017 at the same institution. After one year postdoctoral fellowship supervised by Dr Steve Davies working about in Synthetic Methodolgy with Lithium Amide Conjugate Addition and Total Synthesis at the University of Oxford, UK she obtained the position of an Auxiliar Professor where work actually.