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

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.

SUBMITTER: Pagar VV

PROVIDER: S-EPMC6055924 | biostudies-other | 2018 Jul

REPOSITORIES: biostudies-other

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

Pagar Vinayak Vishnu VV RajanBabu T V TV

Science (New York, N.Y.) 20180701 6397

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. Thes ...[more]

PMID: 29976822

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