Catalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoamides Catalyzed by a Single H‐Bond Donor Organocatalyst
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.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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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)
- Urheber
- DOI
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10.1002/ange.202201788
- URN
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urn:nbn:de:101:1-2022031214094514937520
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:32 MESZ
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Beteiligte
- Andres, Rémi
- Wang, Qian
- Zhu, Jieping
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