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Doctoral thesis
English

Organocatalytic enantioselective construction of mono- and polycyclic structures by domino reactions

Contributors

Lefranc, Alice

Directors

Alexakis, Alexandre

Defense date

2014-06-27

Abstract

In this manuscript, we are particularly interested in the formation of chiral mono- and polycyclic compounds by organocatalytic domino reactions. In order to understand better the studied reactivities, some generalities about the activation modes used during this work, aminocatalysis and bifunctional thiourea-type catalysis, are firlsty introduced. Afterwards, a study on the synthesis of chiral γ-butenolides from renewable sources by a direct vinyligous Michael addition of Angelicalactone to enals catalysed by an aminal-pyrrolidine catalyst is reported. In the third part, we focused on the reactivity of acyclic 1,2-diketones in organocatalytic domino transformations. Interesting chiral polysubstituted cyclopentanones are synthesized by domino reactions. Finally, β,γ-unsaturated 1,2 dicarbonyl compounds are involved in organocatalytic domino tranformations as bis-electrophiles with various cyclic 1,3-ketoesters forming interesting chiral polysubstituted bicyclo[3.2.1]octanones.

Keywords

  • Organocatalysis-Domino
  • Reactions-asymmetric catalysis

UNIGE affiliation entities

UNIGE research groups

Citation (ISO format)

LEFRANC, Alice. Organocatalytic enantioselective construction of mono- and polycyclic structures by domino reactions. Doctoral Thesis, 2014. doi: 10.13097/archive-ouverte/unige:39205

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Technical informations

Creation

22/07/2014 13:03:00

First validation

22/07/2014 13:03:00

Update

14/03/2023 21:30:21

Status update

14/03/2023 21:30:21

Last indexation

13/05/2025 16:36:34
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