Modular Cyclopentenone Synthesis through the Catalytic Molecular Shuffling of Unsaturated Acid Chlorides and Alkynes

Yong Ho Lee, Elliott H. Denton, Bill Morandi

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

We describe a general strategy for the intermolecular synthesis of polysubstituted cyclopentenones using palladium catalysis. Overall, this reaction is achieved via a molecular shuffling process involving an alkyne, an α,β-unsaturated acid chloride, which serves as both the alkene and carbon monoxide source, and a hydrosilane to create three new C-C bonds. This new carbon monoxide-free pathway delivers the products with excellent yields. Furthermore, the regioselectivity is complementary to conventional methods for cyclopentenone synthesis. In addition, a set of regio- and chemodivergent reactions are presented to emphasize the synthetic potential of this novel strategy.

Original languageEnglish
Pages (from-to)20948-20955
Number of pages8
JournalJournal of the American Chemical Society
Volume142
Issue number50
DOIs
Publication statusPublished - 2020 Dec 16
Externally publishedYes

Bibliographical note

Funding Information:
The financial support by the European Research Council under the European Union’s Horizon 2020 research and innovation program (Shuttle Cat, Project ID: 757608), the ETH Zürich, and LG Chem (fellowship to Y.H.L.) is gratefully acknowledged. We thank the NMR, MS (MoBiAS), and X-ray (SMoCC) service departments at ETH Zürich for technical assistance. We are also grateful to Prof. E. M. Carreira for sharing chiral GC and M. Isomura and V. Gerken for technical help.

Publisher Copyright:
© 2020 American Chemical Society.

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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