Asymmetric Catalytic [3+2] Annulation of Donor-Acceptor Cyclopropane with Cyclic Ketones: Facile Access to Enantioenriched 1-Oxaspiro[4.5]decanes

  • Zhong Bo Zheng
  • , Wen Fu Cheng
  • , Lijia Wang*
  • , Jun Zhu
  • , Xiu Li Sun*
  • , Yong Tang*
  • *Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

A copper catalyzed enantioselective [3+2] annulation of donor-acceptor cyclopropanes with cyclic ketones has been developed, providing a concise protocol to enantioenriched 1-oxaspiro[4.5]decanes in up to 98% yield with up to >99/1 dr and up to 92% ee. In addition, this method also provides a facile access to the enantioselective desymmetrisation of various 4-substituted cyclohexanones. The resulting products were easily converted to the core structures of two natural products Heliespirones A and halogenated sesquiterpene isolated from L. saitoi.

Original languageEnglish
Pages (from-to)1629-1634
Number of pages6
JournalChinese Journal of Chemistry
Volume38
Issue number12
DOIs
StatePublished - Dec 2020

Keywords

  • Asymmetric catalysis
  • Copper
  • Cyclic ketones
  • Donor-acceptor cyclopropane
  • [3+2] annulation

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