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

doi:10.1002/adsc.201800575

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 journal › Article

2 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 language	English
Pages (from-to)	3381-3390
Number of pages	10
Journal	Advanced Synthesis and Catalysis
Volume	360
Issue number	17
DOIs	https://doi.org/10.1002/adsc.201800575
Publication status	Published - 2018 Sep 3

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Keywords

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

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Cite this

Chang, C. A., Uang, T. Y., Jian, J. H., Zhou, M. Y., Chen, M. L., Kuo, T. S., Wu, P. Y., & Wu, H. L. (2018). Efficient and Enantioselective Rhodium(I)-Catalyzed Arylation of α-Ketoesters: Synthesis of (S)-Flutriafol. Advanced Synthesis and Catalysis, 360(17), 3381-3390. https://doi.org/10.1002/adsc.201800575

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 journal › Article

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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.).",

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AB - 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.).

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Access to Document

10.1002/adsc.201800575