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 › peer-review

5 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

Keywords

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

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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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 › peer-review

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

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.).",

keywords = "arylation, asymmetric catalysis, rhodium, tertiary α-hydroxy esters, α-ketoesters",

author = "Chang, {Chiung An} and Uang, {Tsung Ying} and Jian, {Jia Hong} and Zhou, {Meng Yi} and Chen, {Ming Liang} and Kuo, {Ting Shen} and Wu, {Ping Yu} and Wu, {Hsyueh Liang}",

note = "Funding Information: We thank Dr. Julian P. Henschke for his input during the preparation of this manuscript. Financial support from the Ministry of Science and Technology of Republic of China (102-2113-M-003-006-MY2 and 104-2628-M-003-001-MY3) is greatly acknowledged.",

year = "2018",

month = sep,

day = "3",

doi = "10.1002/adsc.201800575",

language = "English",

volume = "360",

pages = "3381--3390",

journal = "Advanced Synthesis and Catalysis",

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T1 - Efficient and Enantioselective Rhodium(I)-Catalyzed Arylation of α-Ketoesters

T2 - Synthesis of (S)-Flutriafol

AU - Chang, Chiung An

AU - Uang, Tsung Ying

AU - Jian, Jia Hong

AU - Zhou, Meng Yi

AU - Chen, Ming Liang

AU - Kuo, Ting Shen

AU - Wu, Ping Yu

AU - Wu, Hsyueh Liang

N1 - Funding Information: We thank Dr. Julian P. Henschke for his input during the preparation of this manuscript. Financial support from the Ministry of Science and Technology of Republic of China (102-2113-M-003-006-MY2 and 104-2628-M-003-001-MY3) is greatly acknowledged.

PY - 2018/9/3

Y1 - 2018/9/3

N2 - 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.).

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.).

KW - arylation

KW - asymmetric catalysis

KW - rhodium

KW - tertiary α-hydroxy esters

KW - α-ketoesters

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JO - Advanced Synthesis and Catalysis

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SN - 1615-4150

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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