{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Chan YC"],"funding":["National Institutes of Health","eli lilly and company","NIGMS NIH HHS","NIH HHS","Eli Lilly and Company"],"pagination":["24573-24581"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC8556314"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["60(46)"],"pubmed_abstract":["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."],"journal":["Angewandte Chemie (International ed. in English)"],"pubmed_title":["Tunable and Cooperative Catalysis for Enantioselective Pictet-Spengler Reaction with Varied Nitrogen-Containing Heterocyclic Carboxaldehydes."],"pmcid":["PMC8556314"],"funding_grant_id":["R35 GM132092"],"pubmed_authors":["Frank SA","Sak MH","Chan YC","Miller SJ"],"additional_accession":[]},"is_claimable":false,"name":"Tunable and Cooperative Catalysis for Enantioselective Pictet-Spengler Reaction with Varied Nitrogen-Containing Heterocyclic Carboxaldehydes.","description":"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.","dates":{"release":"2021-01-01T00:00:00Z","publication":"2021 Nov","modification":"2025-04-05T12:34:02.611Z","creation":"2025-04-05T12:34:02.611Z"},"accession":"S-EPMC8556314","cross_references":{"pubmed":["34487418"],"doi":["10.1002/anie.202109694"]}}