Highly enantioselective rhodium-catalyzed asymmetric 1,4-addition reactions of arylboronic acids to acyclic α,β-unsaturated compounds: The formal synthesis of (-)-indatraline

Wei Ting Wei; Jiann Yih Yeh; Ting Shen Kuo; Hsyueh Liang Wu

doi:10.1002/chem.201102073

Highly enantioselective rhodium-catalyzed asymmetric 1,4-addition reactions of arylboronic acids to acyclic α,β-unsaturated compounds: The formal synthesis of (-)-indatraline

Wei Ting Wei, Jiann Yih Yeh, Ting Shen Kuo, Hsyueh Liang Wu^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

56 引文斯高帕斯（Scopus）

摘要

It's do or diene: Stable chiral bicyclo[2.2.1]diene ligands were synthesized from (-)-5-oxobornyl acetate and utilized in the asymmetric 1,4-addition reaction of arylboronic acids with acyclic α,β- unsaturated compounds. Low catalytic loading of the complex, generated in situ from 1 and [{RhCl(C₂H₄)₂}₂], provides adducts in good to excellent yields and excellent enantioselectivities. This method was used for the formal total synthesis of (-)-indatraline.

原文	英語
頁（從 - 到）	11405-11409
頁數	5
期刊	Chemistry - A European Journal
卷	17
發行號	41
DOIs	https://doi.org/10.1002/chem.201102073
出版狀態	已發佈 - 2011 10月 4

ASJC Scopus subject areas

催化
有機化學

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10.1002/chem.201102073

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CCDC 856042: Experimental Crystal Structure Determination
Wei, W. (Creator), Yeh, J. (Creator), Kuo, T. (Creator) & Wu, H. (Creator), Unknown Publisher, 2013
DOI: 10.5517/ccxqs8n, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccxqs8n&sid=DataCite
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Highly enantioselective rhodium-catalyzed asymmetric 1,4-addition reactions of arylboronic acids to acyclic α,β-unsaturated compounds: The formal synthesis of (-)-indatraline. / Wei, Wei Ting; Yeh, Jiann Yih; Kuo, Ting Shen 等.
於: Chemistry - A European Journal, 卷 17, 編號 41, 04.10.2011, p. 11405-11409.

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

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title = "Highly enantioselective rhodium-catalyzed asymmetric 1,4-addition reactions of arylboronic acids to acyclic α,β-unsaturated compounds: The formal synthesis of (-)-indatraline",

abstract = "It's do or diene: Stable chiral bicyclo[2.2.1]diene ligands were synthesized from (-)-5-oxobornyl acetate and utilized in the asymmetric 1,4-addition reaction of arylboronic acids with acyclic α,β- unsaturated compounds. Low catalytic loading of the complex, generated in situ from 1 and [{RhCl(C2H4)2}2], provides adducts in good to excellent yields and excellent enantioselectivities. This method was used for the formal total synthesis of (-)-indatraline.",

keywords = "addition reactions, arylboronic acids, asymmetric catalysis, diene ligands, enantioselectivity, indatraline, rhodium",

author = "Wei, {Wei Ting} and Yeh, {Jiann Yih} and Kuo, {Ting Shen} and Wu, {Hsyueh Liang}",

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T2 - The formal synthesis of (-)-indatraline

AU - Wei, Wei Ting

AU - Yeh, Jiann Yih

AU - Kuo, Ting Shen

AU - Wu, Hsyueh Liang

PY - 2011/10/4

Y1 - 2011/10/4

N2 - It's do or diene: Stable chiral bicyclo[2.2.1]diene ligands were synthesized from (-)-5-oxobornyl acetate and utilized in the asymmetric 1,4-addition reaction of arylboronic acids with acyclic α,β- unsaturated compounds. Low catalytic loading of the complex, generated in situ from 1 and [{RhCl(C2H4)2}2], provides adducts in good to excellent yields and excellent enantioselectivities. This method was used for the formal total synthesis of (-)-indatraline.

AB - It's do or diene: Stable chiral bicyclo[2.2.1]diene ligands were synthesized from (-)-5-oxobornyl acetate and utilized in the asymmetric 1,4-addition reaction of arylboronic acids with acyclic α,β- unsaturated compounds. Low catalytic loading of the complex, generated in situ from 1 and [{RhCl(C2H4)2}2], provides adducts in good to excellent yields and excellent enantioselectivities. This method was used for the formal total synthesis of (-)-indatraline.

KW - addition reactions

KW - arylboronic acids

KW - asymmetric catalysis

KW - diene ligands

KW - enantioselectivity

KW - indatraline

KW - rhodium

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Highly enantioselective rhodium-catalyzed asymmetric 1,4-addition reactions of arylboronic acids to acyclic α,β-unsaturated compounds: The formal synthesis of (-)-indatraline

摘要

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資料集

CCDC 856042: Experimental Crystal Structure Determination

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