Stereoselective Transformations of Vinyl Cyclic Carbonates and Applications in Natural Product Synthesis

Identifier:  TDX:3811

Handle: https://hdl.handle.net/20.500.11797/TDX3811

Authors:  Cristòfol Martínez, Àlex

Abstract:
Finding new strategies to forge carbon-carbon bonds has become fundamental to synthesize complex molecules rapidly and efficiently. The aim of this doctoral thesis is to devise novel catalytic and stereoselective methods for the construction of such carbon-carbon bonds using vinyl cyclic carbonates to build more elaborate molecules with potential application for the synthesis of natural products and pharmaceuticals. A highly (Z)-selective palladiumcatalyzed allylation of nitroalkanes is presented, which is utilized to examine the synthesis of biologically active indolizidine and quinolizidine natural products. In addition, a combined approach towards the allylation of aldehydes merging cobalt and photoredox catalysis is introduced. The combined experimental results from this thesis showcase how vinyl cyclic carbonates can be effectively reacted under the influence of a transition metal catalyst to forge strategic carbon-carbon bonds that allow the synthesis of more elaborated motifs and natural products. The extent of this work will likely help revitalize the use of such scaffolds in more modern synthetic campaigns and method development.