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Hydroalkynylative cyclization of 1,6-enynes with terminal alkynes.

ABSTRACT: A rhodium-catalyzed highly regio- and enantioselective hydroalkynylation, generating cis-hydrobenzofuranone-tethered enynes has been developed. The reaction proceeds with a selective head-to-head insertion and symmetry breaking Michael addition cascade. One product was produced from tens of possible isomers through precise control of chemo-, regio-, and stereoselectivities using a single rhodium catalyst. Notable features of this method include 100% atom-economy, mild reaction conditions and a very broad substrate scope.

SUBMITTER: Teng Q

PROVIDER: S-EPMC6657412 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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Hydroalkynylative cyclization of 1,6-enynes with terminal alkynes.

Teng Qi Q Thirupathi Nuligonda N Tung Chen-Ho CH Xu Zhenghu Z

Chemical science 20190613 28

A rhodium-catalyzed highly regio- and enantioselective hydroalkynylation, generating <i>cis</i>-hydrobenzofuranone-tethered enynes has been developed. The reaction proceeds with a selective head-to-head insertion and symmetry breaking Michael addition cascade. One product was produced from tens of possible isomers through precise control of chemo-, regio-, and stereoselectivities using a single rhodium catalyst. Notable features of this method include 100% atom-economy, mild reaction conditions ...[more]

PMID: 31391909

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