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Enantioselective formal

Wermeskerken, J. van (2010) Enantioselective formal. Bachelor's Thesis, Industrial Engineering and Management.

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During the 14 weeks of bachelor research a formal aza-Diels-Alder reaction was investigated. The reason for investigating this reaction is that the product, a pyridone, is an important building block in natural product synthesis and pharmaceutical products. This copper(I) catalyzed reaction also requires catalytic amounts of silver(I) and of course a chiral ligand in order to make the reaction enantioselective. Starting with different N-tosylimines using the chiral ligand Josiphos, electronic effects on the reaction were studied, resulting in ee’s up to 78%. The isolated yields were usually around 60-80%. Next to this, four other chiral ligands, 3 phosphoramidites and Taniaphos, were used as well to see their performance in the reaction. In this case only Taniaphos resulted in a moderate ee of 54%.Also the influence of temperature was taken a brief look at, by lowering the temperature from RT to 0°C.

Item Type: Thesis (Bachelor's Thesis)
Degree programme: Industrial Engineering and Management
Thesis type: Bachelor's Thesis
Language: English
Date Deposited: 15 Feb 2018 07:44
Last Modified: 15 Feb 2018 07:44

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