Efficient and Enantioselective Rhodium(I)-Catalyzed Arylation of α-Ketoesters: Synthesis of (S)-Flutriafol

Chiung An Chang, Tsung Ying Uang, Jia Hong Jian, Meng Yi Zhou, Ming Liang Chen, Ting Shen Kuo, Ping Yu Wu, Hsyueh Liang Wu

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

An enantioselective addition of arylboronic acids and α-ketoesters promoted by a Rhodium(I)-chiral diene catalyst is reported. The transformation proceeds regioselectively in the presence of as low as 0.5 mol% of the catalyst generated in situ from a Rhodium(I) salt and diene L1, which is a bicyclo[2.2.1] ligand scaffold bearing 2,5 dinaphthyl substituents, to afford tertiary chiral α-hydroxy esters with high stereoselectivities (90–99% ee's) and in 50–>99% yields. The method provides an expeditious and enantioselective synthesis of (S)-flutriafol. (Figure presented.).

Original languageEnglish
Pages (from-to)3381-3390
Number of pages10
JournalAdvanced Synthesis and Catalysis
Volume360
Issue number17
DOIs
Publication statusPublished - 2018 Sep 3

Keywords

  • arylation
  • asymmetric catalysis
  • rhodium
  • tertiary α-hydroxy esters
  • α-ketoesters

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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