Enantioselective Organocatalyzed Functionalization of Tetramic and Tetronic Acids

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Abstract: Organocatalyzed Michael addition of N‐substituted tetramic acids to nitroalkene acceptors followed by O‐alkylation gave polyfunctionalized tetramic acid (31 examples, 59–94% ee). The enantioselectivity of the product was influenced by the N‐substituent of the substrate. Quantum chemical methods provided the mechanistic insights of the studied transformation. The preferred reaction pathway follows the model proposed by Pápai et al. Single crystal structure confirmed the absolute configuration, which was in line with the ECD measured and calculated structure. Additionally, a comparative study of the alkylation of a selected tetramic and tetronic acid with trans‐β‐nitrostyrene is disclosed. Follow‐up amidations demonstrated the applicability of this class of compounds for the incorporation into both dipeptide and depsipeptide sequences.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Enantioselective Organocatalyzed Functionalization of Tetramic and Tetronic Acids ; day:26 ; month:10 ; year:2022 ; extent:1
Advanced synthesis & catalysis ; (26.10.2022) (gesamt 1)

Creator: Ciber, Luka
Gorenc, Ana
Hozjan, Mišel
Požgan, Franc
Svete, Jurij
Brodnik, Helena
Štefane, Bogdan
Grošelj, Uroš

DOI: 10.1002/adsc.202200810

URN: urn:nbn:de:101:1-2022102715214909134088

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:37 AM CEST

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Ciber, Luka
Gorenc, Ana
Hozjan, Mišel
Požgan, Franc
Svete, Jurij
Brodnik, Helena
Štefane, Bogdan
Grošelj, Uroš

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Enantioselective Organocatalyzed Functionalization of Tetramic and Tetronic Acids

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