Catalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoamides Catalyzed by a Single H‐Bond Donor Organocatalyst

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Abstract: The asymmetric Pictet–Spengler reaction (PSR) with aldehydes is well known. However, PSR involving ketones as electrophilic partners is far‐less developed. We report herein the first examples of catalytic enantioselective PSR of tryptamines with α‐ketoamides. A new class of easily accessible prolyl‐urea organocatalysts bearing a single H‐bond donor function catalyzes the title reaction to afford 1,1‐disubstituted tetrahydro‐β‐carbolines in excellent yields and enantioselectivities. The kinetic isotope effect using C2‐deuterium‐labelled tryptamine indicates that the rearomatization of the pentahydro‐β‐carbolinium ion intermediate might be the rate‐ and the enantioselectivity‐determining step.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Catalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoamides Catalyzed by a Single H‐Bond Donor Organocatalyst ; day:11 ; month:03 ; year:2022 ; extent:1
Angewandte Chemie ; (11.03.2022) (gesamt 1)

Creator: Andres, Rémi
Wang, Qian
Zhu, Jieping

DOI: 10.1002/ange.202201788

URN: urn:nbn:de:101:1-2022031214094514937520

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

Last update: 15.08.2025, 7:32 AM CEST

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Andres, Rémi
Wang, Qian
Zhu, Jieping

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