Catalyse stéréosélective de nouvelles réactions tandems basées sur des complexes de cuivre (I)
(2010)
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- Authors
- Supervisors
- Riant, Olivier
- Abstract
- (en) Domino reactions are processes that allow sparing considerable work. These reactions have been applied among other to reductive aldol type processes based on copper catalysts. The aim of this thesis consists in the pursuit of this work by prospecting new applications. The first part of this work is dedicated to the study of tandem reductive aldol reactions based on copper-phosphorus complexes. However, many problems of reactivity, of chemo-, diastéréo- and enantioselectivities were met and no viable solution could be found. Concerning the use of diaminocarbenes as ligand, we obtained excellent results, good yields and interesting diastereoselectivities and especially high activities and chemoselectivities. Air-stable complexes that do not require activation were developed. The introduction of a boronic ester and a silyl group were then studied. The catalytic system tolerates a vast variety of different electrophiles and Michael acceptors. In both cases, the chemoselectivity is complete and yields are good. However, diastereoselectivities are usually nul or low excepted in particular cases. With silylated compounds, the control of the stereochemistry of formed centres can be assured by using a chiral auxiliary. Moreover, it is possible to form a chiral quaternary centre in a stereocontrolled way.
- Affiliations
Citations
Welle, A. (2010). Catalyse stéréosélective de nouvelles réactions tandems basées sur des complexes de cuivre (I). https://hdl.handle.net/2078.5/129507