From Racemic to Enantioselective Total Synthesis of Trigonoliimines via Development of an Organocatalytic Enantioselective Michael Addition of α-Aryl-α-isocyanoacetate to Vinyl Phenyl Selenone
Aliphatic alkynes and nitriles are privileged motifs in organic chemistry. Therefore, alkynes and nitriles have played a central role for the exploration and development of novel strategies to forge C-C bonds in efficient manner. They are broadly used as v ...
Cp*Ir(III) catalyzed C-H functionalization is a growing field, since it provides novel complementary reactivities, but enantioselective C-H functionalization reactions with this metal remain a niche. This thesis investigates CpXIr(III) catalyzed asymmetric ...
The total synthesis of pentacyclic monoterpene indole alkaloids is the focus of this thesis.
Total syntheses of (±)-alstilobanine C, (±)-undulifoline and (±)-alstilobanine B, three natural products from the Ulean family of alkaloids, were accomplished. The ...
The chemistry of aromatic triazenes is well known, and has been explored for more than a century.
These compounds have emerged as very useful intermediates, because of their unique reactivity.
This functionality can notably be used to access many other fun ...
Amines are a quintessential moiety in bioactive molecules, pharmaceuticals and organic materials. Transition-metal-catalysed C–N coupling of aryl electrophiles has been established as a powerful and reliable method for amine synthesis. However, the analogo ...
Carbo- and heterocyclic structures containing nitrogen-substituted stereocenters are recurrent structural motifs in natural and bioactive compounds, therefore constituting a privileged class of synthetic targets. In this regard, substituted three- and four ...
An enantioselective total synthesis of (-)-terengganensine A, a heptacyclic monoterpene indole alkaloid, was performed. A short sequence allowed to obtain the enantio-enriched target in good overall yield. The synthesis featured a key asymmetric transfer h ...
In the presence of a catalytic amount of chiral phosphoric acid, nucleophilic addition of N-monosubstituted hydrazones to N-Boc imines affords differentially protected vicinal diamines in the form of b-amino N,N’-dialkyldiazenes in excellent yields with hi ...
Alkene functionality can be found in the majority of natural products, drugs, catalysts and organic materials. Therefore, methods of C-C double bond formation constitute a cornerstone of organic synthesis. Selective formation of either (Z)- or (E)-isomer i ...
Many abundant and highly bioactive natural alkaloids contain an indolizidine skeleton. A simple, high yielding method to synthesize this scaffold from N-heterocycles was developed. A wide range of pyridines, quinolines and isoquinolines reacted with donor- ...
A novel Cinchona alkaloid-catalyzed enantioselective conjugate addition of alpha-alkyl substituted alpha-nitroacetates to phenyl vinyl selenone was developed. The resulting enantio-enriched alpha,alpha-dialkyl substituted alpha-nitroacetates were subsequen ...
Thiol-ene addition of thioacetic acid A is widely used in the synthesis of thiols from vinyl precursors, but so far has not been conducted on non-conjugated vinyl nitriles. The challenge when vinyl nitriles are used is to selectively conduct the thiol-ene ...
