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

1 Citation (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

Fingerprint

Rhodium
Bearings (structural)
Stereoselectivity
Catalysts
Scaffolds
Esters
Salts
Ligands
Acids
flutriafol

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Efficient and Enantioselective Rhodium(I)-Catalyzed Arylation of α-Ketoesters : Synthesis of (S)-Flutriafol. / Chang, Chiung An; Uang, Tsung Ying; Jian, Jia Hong; Zhou, Meng Yi; Chen, Ming Liang; Kuo, Ting Shen; Wu, Ping Yu; Wu, Hsyueh Liang.

In: Advanced Synthesis and Catalysis, Vol. 360, No. 17, 03.09.2018, p. 3381-3390.

Research output: Contribution to journalArticle

Chang, Chiung An ; Uang, Tsung Ying ; Jian, Jia Hong ; Zhou, Meng Yi ; Chen, Ming Liang ; Kuo, Ting Shen ; Wu, Ping Yu ; Wu, Hsyueh Liang. / Efficient and Enantioselective Rhodium(I)-Catalyzed Arylation of α-Ketoesters : Synthesis of (S)-Flutriafol. In: Advanced Synthesis and Catalysis. 2018 ; Vol. 360, No. 17. pp. 3381-3390.
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