Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C3-Chirogenic Center

Chong Liu, Jing Yuan, Zhenfeng Zhang, Ilya D. Gridnev, Wanbin Zhang

Research output: Contribution to journalArticlepeer-review

Abstract

A new transformation pattern for enantioselective intramolecular hydroacylation has been developed involving an alkene isomerization strategy. Proceeding through a five-membered rhodacycle intermediate, 3-enals were converted to C3- or C3,C5-chirogenic cyclopentanones with satisfactory yields, diastereoselectivities, and enantioselectivities. A catalytic cycle has been theoretically calculated and the origin of the stereoselection is rationally explained.

Original languageEnglish
Pages (from-to)8997-9002
Number of pages6
JournalAngewandte Chemie - International Edition
Volume60
Issue number16
DOIs
Publication statusPublished - 2021 Apr 12

Keywords

  • alkene isomerization
  • cycloketones
  • hydroacylation
  • rhodacycle
  • β-H elimination

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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