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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
Ασύμμετρη σύνθεση
Issue date 2020-03-27
Collection   Faculty/Department--Faculty of Sciences and Engineering--Department of Chemistry--Post-graduate theses
  Type of Work--Post-graduate theses
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