Unit:
Κατεύθυνση Οργανική Σύνθεση και Εφαρμογές της στη Χημική ΒιομηχανίαLibrary of the School of Science
Author:
Θεοδώρου Αλέξιος-Νικόλαος
Supervisors info:
Παναγιώτα Μουτεβελή-Μηνακάκη Αναπλ. Καθηγήτρια ΕΚΠΑ (Επιβλέπουσα), Γεώργιος Κόκκοτος Καθηγητής ΕΚΠΑ, Δημήτριος Γεωργιάδης Επίκ. Καθηγητής ΕΚΠΑ
Original Title:
Σύνθεση α, α-Διυποκατεστημένων Αλδεϋδών και Οργανοκαταλυτική Μέθοδος Σύνθεσης α, α-Διυποκατεστημένων Αμινοξέων
Translated title:
Synthesis of α,α-disubstituted aldehydes and organocatalytic method of synthesis of α,α-disubstituted aminoacids
Summary:
In chapter 1, an introduction in organocatalysis and its main advantages are
described. The existing modes of activation in organocatalysis as well as some
representative examples of the enamine activation mode are discussed.
Furthermore, a detail analysis of the enantioselective α-amination of α-
substituted aldehydes and α,α-disubstituted aldehydes is given.The second
chapter presents the aim of the current thesis, which is the identification of
the appropriate α-amino acid derivative that can efficiently catalyse the
organocatalytic reaction between α,α-disubstituted aldehyde and the di-alkyl
azocarboxylates. In chapter 3, the synthesis and the mechanistic aspects of the
synthesis of α,α-disubstituted aldehydes are presented. After identification of
β-tert-butyl-aspartate as the best catalyst for the reaction between α,α-
disubstituted aldehyde and the di-alkyl azocarboxylates, the optimum reaction
conditions and the substrate scope of the reaction were studied. Moreover, the
transformation of the organocatalytic product to a protected derivative of α,α-
disubstituted amino acid was carried out. Finally, the spectroscopic data were
quoted.The fourth chapter describes all the experimental and spectroscopic data
of all the substrates and products that were synthesized in this thesis.
Keywords:
α, α-Disubstituted aldehydes, α, α-Disubstituted aminoacids, Οrganocatalysis, α-Amination, Εnamine
Number of index pages:
7-11
