Tunable and Cooperative Catalysis for Enantioselective Pictet-Spengler Reaction with Varied Nitrogen-Containing Heterocyclic Carboxaldehydes.
Pictet-Spengler
cooperative catalysis
heterocycles
hydrogen bond donors
peptides
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
08 11 2021
08 11 2021
Historique:
revised:
24
08
2021
received:
20
07
2021
pubmed:
7
9
2021
medline:
15
12
2021
entrez:
6
9
2021
Statut:
ppublish
Résumé
Herein we report an organocatalytic enantioselective functionalization of heterocyclic carboxaldehydes via the Pictet-Spengler reaction. Through careful pairing of novel squaramide and Brønsted acid catalysts, our method tolerates a breadth of heterocycles, enabling preparation of a series of heterocycle conjugated β-(tetrahydro)carbolines in good yield and enantioselectivity. Careful selection of carboxylic acid co-catalyst is essential for toleration of a variety of regioisomeric heterocycles. Utility is demonstrated via the three-step stereoselective preparation of pyridine-containing analogues of potent selective estrogen receptor downregulator and U.S. FDA approved drug Tadalafil.
Identifiants
pubmed: 34487418
doi: 10.1002/anie.202109694
pmc: PMC8556314
mid: NIHMS1738955
doi:
Substances chimiques
Aldehydes
0
Benzaldehydes
0
Carbolines
0
Carboxylic Acids
0
Heterocyclic Compounds
0
3-pyridinaldehyde
840R4IDQ1T
Nitrogen
N762921K75
benzaldehyde
TA269SD04T
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
24573-24581Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM132092
Pays : United States
Organisme : NIH HHS
ID : R35 GM132092
Pays : United States
Organisme : eli lilly and company
Informations de copyright
© 2021 Wiley-VCH GmbH.
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