Κατεύθυνση Οργανική Χημεία
Library of the School of Science

2016-10-19

2016

Σφέτσα Μαρία

Μηνακάκη-Μουτεβελή Παναγιώτα Καθηγήτρια (Επιβλέπουσα), Κόκοτος Χριστόφορος Επίκ. Καθηγητής, Μαγκριώτη Βικτωρία Επίκ. Καθηγήτρια

Σύνθεση νέων αμιδικών ενώσεων παραγώγων της 2-πυρρολιδινόνης και μελέτη της οργανοκαταλυτικής τους δράσης

Greek

Synthesis of new amide compounds derivatives of 2-pyrrolidinone and the study of their organocatalytic properties

In the present thesis, the synthesis of four new peptide-like compounds is
described and the study of their organocatalytic properties in direct aldol
reaction was performed.
Τhe study of these peptides as organocatalysts revealed that the tripeptide
III afforted the best results concerning the yield of the aldol reaction (~
100%), the diastereoselectivity (up to 97:3%) and enantioselectivity (up to
99%), combined with the fact that the reaction is performed in aqueous
solutions.
Compound I gave equally good results, especially in organic solvent in the
presence of water, and proved that the inversion of the stereogenic center of
phenylalanine from (S) to (R) does not significantly affect its action as
organocatalyst.
The compound II also gave a very good yield and good stereoselectivity mainly
in aqueous media which demonstrated that derivatives of 2-pyrrolidinone (R or
S), as the third amino acid affects the overall configuration of the entire
molecule which of course influences their activity as organocatalysts.
The study of the compound IV as organocatalyst in aqueous media demonstrated
very good stereoselectivity although the yield of the reaction products was not
too high.

Aldol reaction, Tripeptides, 2-pyrrolidinone, Organocatalysts, Proline

Yes

1-7

Yes

78

140

File access is restricted.

https://pergamos.lib.uoa.gr/uoa/dl/object/1320069