Chiral brønsted acid-catalyzed formal α-vinylation of cyclopentanones for the enantioselective construction of quaternary carbon centers

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Abstract

An enantioselective formal α-vinylation of ketones for the construction of an all-carbon quaternary center was established using the vinylogous Wagner-Meerwein shift through the activation of the leaving group by a chiral phosphoramide as the chiral Brønsted acid catalyst. The present reaction afforded enantioenriched all-carbon quaternary α-vinyl ketones in high yields with high enantioselectivities in most cases. Experimental elucidation of the reaction mechanism suggested that the discrimination of the two prochiral faces of the positively charged allylic species and of the enantiotopic migrating groups was efficiently achieved by the chiral phosphoramide catalyst.

Original languageEnglish
Pages (from-to)6846-6850
Number of pages5
JournalACS Catalysis
Volume9
Issue number8
DOIs
Publication statusPublished - 2019 Aug 2

Keywords

  • Wagner-Meerwein shift
  • chiral Brønsted acid
  • quaternary stereogenic center
  • vinylogous
  • α-vinyl ketones

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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