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Content archived on 2024-06-11

Asymmetric nucleophilic alkenoylation with metalated chiral aminonitriles


Research objectives and content
The proposed research sets out to continue the investigation into the use of reversed polarity reagents bearing chiral auxiliaries in the asymmetric synthesis of 1,2- and 1,4-difunctionlised materials as building blocks for organic synthesis.
Enders has recently demonstrated that metalated aminonitriles, derived from aldehydes, and bearing a chiral auxiliary at the amino group, undergo highly diastereoselective 1,4-nucleophilic additions to (a,_)-unsaturated ketones. It is proposed to expand on this methodology by investigating the use of enantiomerically pure metalated aminonitriles derived from (a,_)-unsaturated aldehydes, in additions to both aldehydes and (a,_)-unsaturated carbonyl compounds, in order to access 1,2- and 1,4-difunctionalised materials in high enantiomeric excess. This would provide a useful method for generating chiral alkenoyl anion synthon equivalents
It will be necessary to investigate the influence of steric and electronic factors on the regioselectivity of additions by these ambident nucleophiles as alkenoyl anion or homoenolate equivalents
In addition, it will be necessary to determine the diastereoselectivity of the addition reactions of the alalkenoyl anion equivalents and the enantiomeric purity of their hydrolysis products - expected to be 1,2- and 1,4-difunctionalised ketones.
Training content (objective, benefit and expected impact)
The opportunity to carry out this research will allow the further development of skills and ideas in asymmetric synthesis and organic synthesis in general. The research team at RWTH can provide the facilities and the experience needed to achieve high standards in training. Links with industry / industrial relevance (22)
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EU contribution
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