"Tunable and Cooperative Catalysis for Enantioselective Pictet-Spengler Reaction with Varied Nitrogen-Containing Heterocyclic Carboxaldehydes"

Angew Chem Int Ed Engl. 2021 Sep 6. doi: 10.1002/anie.202109694. Online ahead of print.ABSTRACT"Herein we report an organocatalytic enantioselective functionalization of heterocyclic carboxaldehyde via Pictet-Spengler reaction. Through careful pairing of novel squaramide and Broensted acid catalysts, our method tolerates a breadth of heterocycles, enabling preparation of a series of heterocycle conjugated beta-(tetrahydro)carboline 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 US FDA approved drug Tadalafil."PMID:34487418 | DOI:10.1002/anie.202109694

Source: Angewandte Chemie - September 6, 2021 Category: Chemistry Authors: Yuk-Cheung Chan Marcus H Sak Scott A Frank Scott J Miller Source Type: research