Copper(I)-catalyzed asymmetric decarboxylative Mannich reaction enabled by acidic activation of 2H-azirines.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 30979892.
- Also identified by DOI 10.1038/s41467-019-09750-5 and PMC identifier 6461707.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
Abstract
Chiral aziridines are structure units found in many biologically active compounds and are important building blocks in organic synthesis. Herein, by merging nucleophilic generation through copper(I)-catalyzed decarboxylation and activation of poorly electrophilic 2H-azirines through protonation with carboxylic acids, an asymmetric decarboxylative Mannich reaction between α,α-disubstituted cyanoacetic acids and 2H-azirines is uncovered, which leads to generation of chiral aziridines containing vicinal tetrasubstituted and acyclic quaternary stereogenic carbon centers in good to excellent diastereo- and enantioselectivities. At last, transformations of the produced chiral aziridine are successfully carried out to deliver synthetically useful compounds.