Effect of the enamine pyramidalization direction on the reactivity of secondary amine organocatalysts
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2020-02-21
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Journal Article
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Abstract
Chiral secondary amines are valuable catalysts for reactions that proceed through an enamine intermediate. Here, we explored the importance of the pyramidalization direction of the enamine-N on the reactivity of chiral enamines with a combination of computational, NMR spectroscopic, and kinetic experiments. Studies with peptidic catalysts that bear cyclic amines with different ring sizes revealed that endo-pyramidalized enamines are significantly more reactive compared to exo-pyramidalized analogs. The results show that the pyramidalization direction can have a greater effect than n→π* orbital overlap on the reactivity of chiral enamines. The data enabled the development of a catalyst with higher reactivity compared to the parent catalyst.
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published
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11 (7)
Pages / Article No.
1943 - 1947
Publisher
Royal Society of Chemistry
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Organisational unit
03940 - Wennemers, Helma / Wennemers, Helma
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Funding
169423 - Bioinspirierte Asymmetrische Katalyse (Fortsetzung) (SNF)