Tandem catalysis for asymmetric coupling of ethylene and enynes to functionalized cyclobutanes

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 re...

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Bibliographic Details
Published in:Science (American Association for the Advancement of Science) 2018-07, Vol.361 (6397), p.68-72
Main Authors: Pagar, Vinayak Vishnu, RajanBabu, T V
Format: Article
Language:English
Subjects:
Carbon
Carbon cycle
Cascade chemical reactions
Catalysis
Catalysts
Chemical bonds
Chemical synthesis
Cobalt
Coupling (molecular)
Enantiomers
Ethylene
Fossil fuels
Molecular chains
Natural products
Organic chemistry
Pharmaceuticals
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Summary: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.
ISSN:0036-8075
1095-9203
DOI:10.1126/science.aat6205