Synthesis of bridged tricyclo[5.2.1.0<sup>1,5</sup>]decanes via nickel-catalyzed asymmetric domino cyclization of enynones.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 32312990.
- Also identified by DOI 10.1038/s41467-020-15837-1 and PMC identifier 7171102.
- 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
The restricted availability, expense and toxicity of precious metal catalysts such as rhodium and palladium challenge the sustainability of synthetic chemistry. As such, nickel catalysts have garnered increasing attention as replacements for enyne cyclization reactions. On the other hand, bridged tricyclo[5.2.1.0<sup>1,5</sup>]decanes are found as core structures in many biologically active natural products; however, the synthesis of such frameworks with high functionalities from readily available precursors remains a significant challenge. Herein, we report a nickel-catalyzed asymmetric domino cyclization reaction of enynones, providing rapid and modular synthesis of bridged tricyclo[5.2.1.0<sup>1,5</sup>]decane skeletons with three quaternary stereocenters in good yields and remarkable high levels of regio- and enantioselectivities (92-99% ee).