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Identifier

000429863

Title

Οργανοκαταλυόμενη ασύμμετρη προσθήκη 2-κυκλοεξενονών σε 2-ενάλες και σύνθεση 3-ακυλο-5-αλκοξυβουτυρολακταμών από φουράνια

Alternative Title

Organocatalyzed asymmetric addition of 2-cyclohexenones to 2-enals and synthesis of 3-acyl-5-alkoxybutyrolactams from furans

Author

Σαρρής, Ιωάννης Εμ.

Thesis advisor

Βασιλικογιαννάκης, Γεώργιος

Reviewer

Κατερινόπουλος, Χαράλαμπος
Στρατάκης, Εμμανουήλ

Abstract

In this thesis, two methodologies for the synthesis of highly valuable molecular frameworks are presented. In chapter 1, a synthetic methodology for the production of 3-acyl-5-alkoxy butyrolactams from substituted furans is presented. Photooxygenation of simple furans, with methylene blue acting as sensitizer, was followed by the addition of ammonia or primary amines. The resulting 2-pyrrolidinones were subsequently oxidized by a process where methylene blue acts as a radical initiator in dark, with triplet oxygen being the terminal oxidant. Acidic alcoholysis and oxidation by Dess-Martin periodinane of the resulting 5-hydroxy-butyrolactams furnished the desired 3-acyl-5-alkoxy-butyrolactam products. In chapter 2, a synthetic methodology for the asymmetric construction of bicycle[4,4,0]decane frameworks is presented. This method employs a proline catalyst for the asymmetric LUMO-activation of α,β-unsaturated aldehydes. These dielectronphiles were subjected to two sequential vinylogous additions from the γ and γ’- positions of an appropriately substituted ketoester. A regioselective vinylogous Michael addition from the γ position followed by a vinylogous intramolecular aldol from the γ’ position introduced the [3+3]-annulation product with remarkable regio- and enantioselectivity.

Language

Greek

Subject

Assymetric synthesis

One-pot synthesis

Organocatalysis

Ασύμμετρη σύνθεση

Οργανοκατάλυση

Issue date

2020-03-27

Collection

School/Department--School of Sciences and Engineering--Department of Chemistry--Post-graduate theses