search query: @instructor Joensuu, Pekka / total: 10
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Author: | Gillard, Laurent |
Title: | Organocatalytic enantioselective Robinson annulation |
Publication type: | Final Project work |
Publication year: | 2013 |
Pages: | 50 s. + liitt. 84 Language: eng |
Department/School: | Kemian laitos |
Main subject: | Orgaaninen kemia (Kem-4) |
Supervisor: | Koskinen, Ari |
Instructor: | Joensuu, Pekka |
OEVS: | Electronic archive copy is available via Aalto Thesis Database.
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Location: | P1 Ark Aalto 2111 | Archive |
Abstract (eng): | The aim of the research was to find a catalytic and enantioselective way for the Robinson annulation reaction, our target molecule is the aspidospermine. The use of amino-acid is really useful in enamine chemistry, because they are chiral amino-compounds and can be easily substituted. Several primary and secondary amines were used as catalyst and a plethora of conditions were used to achieve this reaction. It was observed that the relativities of primary and secondary amine were really different indicated their mechanisms are different. No catalytic way to perform the reaction was found. It was improved and now this path allows us to reach 88% of the desired product. The catalytic way was developed with a sterically hindered catalyst. However, the conditions to achieve this are not the best. Attempts were performed to improve it, without any success. The enantioselectivities reached by those catalysts was low. The discovery of a possible interaction between the function of the catalyst and the enantioselectivity was established. However only low enantiomer excess was developed. The options are extensive, even if no very good e.e was achieved; there are still lots of opportunities in this field of research. |
ED: | 2013-08-07 |
INSSI record number: 47035
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