Tandem catalysis for asymmetric coupling of ethylene and enynes to functionalized cyclobutanes.
basic_science · Level V
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- Record sourced from PubMed, PMID 29976822.
- Also identified by DOI 10.1126/science.aat6205 and PMC identifier 6055924.
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Abstract
Transformation of simple precursors into structurally complex cyclobutanes, present in many biologically important natural products and pharmaceuticals, is of considerable interest in medicinal chemistry. Starting from 1,3-enynes and ethylene, both exceptionally inexpensive starting materials, we report a cobalt-catalyzed route to vinylcyclobutenes, as well as the further enantioselective addition of ethylene to these products to form complex cyclobutanes with all-carbon quaternary centers. These reactions can proceed in discrete stages or in a tandem fashion to achieve three highly selective carbon-carbon bond formations in one pot using a single chiral cobalt catalyst.