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Peer-reviewed
Jun 11, 2020

Carbamate as an accelerating group in intermolecular Pauson-Khand reaction

Tetrahedron Letters
  • Shota Asano
  • ,
  • Kaori Itto-Nakama
  • ,
  • Hirokazu Arimoto

Volume
61
Number
24
Language
Publishing type
Research paper (scientific journal)
DOI
10.1016/j.tetlet.2020.151974

© 2020 Elsevier Ltd The Pauson-Khand reaction (PKR) is a powerful means for the construction of cyclopentenones. However, its applications have been limited to the intramolecular version of this reaction because poor yield and regioselectivity are often the major problems in intermolecular PKR. Here we describe that a carbamate moiety in alkene substrate accelerates this intermolecular PKR. The reaction of N-4-dimethylaminophenyl O-allyl carbamate with alkyne-cobalt complex gave cyclopentenones in high yield (up to 90%) and regioselectivity (>9:1).

Link information
DOI
https://doi.org/10.1016/j.tetlet.2020.151974
Scopus
https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85084066798&origin=inward
Scopus Citedby
https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85084066798&origin=inward
ID information
  • DOI : 10.1016/j.tetlet.2020.151974
  • ISSN : 0040-4039
  • eISSN : 1873-3581
  • SCOPUS ID : 85084066798

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