Construction d'hétérocycles azotés par hydroamination intramoléculaire d'oléfines
(2009)
Files
THESE-CQuinet.pdf
Open Access - Adobe PDF
- 3.72 MB
Details
- Authors
- Supervisors
- Markó, Istvan
- Abstract
- (en) Our laboratory has developed a simple, efficient and cheap method, based upon the intramolecular hydroamination of olefins, for the synthesis of nitrogen heterocycles. These amines are ubiquitous subunits in a wide variety of biologically active alkaloids. A catalytic amount of n-butyllithium or of an in situ generated samarium complex (SmI2 or SmI3 / NaN(TMS)2) induces the cyclisation of aminoolefins. We have observed important solvent and temperature effects. Finally, we have successfully applied our two protocols to the synthesis of a natural compound, (±)-Dihydropinidine. In the second part of our work, we have studied the intramolecular hydroamination of vinylsulfides. These hydroamination reactions enabled the efficient synthesis of various nitrogen monocycles and bicycles. Functionalised nitrogen heterocycles have then been obtained by subsequent transformations of the sulfur group. This approach demonstrates the major interest of our new methodology and offers rich and varied perspectives for the synthesis of a wide variety of alkaloids.
- Affiliations
Citations
Quinet, C. (2009). Construction d’hétérocycles azotés par hydroamination intramoléculaire d’oléfines. https://hdl.handle.net/2078.5/131085