Organocatalytic enantioselective Robinson annulation

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Journal Title

Journal ISSN

Volume Title

School of Chemical Engineering |

Authors

Date

2013

Department

Kemian laitos

Major/Subject

Orgaaninen kemia

Mcode

Kem-4

Degree programme

Language

en

Pages

50 s. + liitt. 84

Series

Abstract

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.

Description

Supervisor

Koskinen, Ari

Thesis advisor

Joensuu, Pekka

Keywords

Other note

Citation

Permanent link to this item

https://urn.fi/URN:NBN:fi:aalto-202108318755

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