Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 19, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202201788
Keywords
Asymmetric Synthesis; Organocatalysis; Pictet-Spengler Reaction; Tetrahydrocarbazole; alpha-Oxoamides
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Funding
- EPFL (Switzerland)
- Swiss National Science Foundation [SNSF 200020-169077]
- Ecole Polytechnique Federale de Lausanne
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This paper reports the first examples of catalytic enantioselective PSR of tryptamines with alpha-ketoamides, and a new class of easily accessible organocatalysts was developed to achieve excellent yields and enantioselectivities.
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 alpha-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-beta-carbolines in excellent yields and enantioselectivities. The kinetic isotope effect using C2-deuterium-labelled tryptamine indicates that the rearomatization of the pentahydro-beta-carbolinium ion intermediate might be the rate- and the enantioselectivity-determining step.
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