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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

60 Citations (Scopus)

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.

Original language	English
Pages (from-to)	11405-11409
Number of pages	5
Journal	Chemistry - A European Journal
Volume	17
Issue number	41
DOIs	https://doi.org/10.1002/chem.201102073
Publication status	Published - 2011 Oct 4

Keywords

addition reactions
arylboronic acids
asymmetric catalysis
diene ligands
enantioselectivity
indatraline
rhodium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201102073

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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 et al.
In: Chemistry - A European Journal, Vol. 17, No. 41, 04.10.2011, p. 11405-11409.

Research output: Contribution to journal › Article › peer-review

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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.",

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AU - Yeh, Jiann Yih

AU - Kuo, Ting Shen

AU - Wu, Hsyueh Liang

PY - 2011/10/4

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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

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 856042: Experimental Crystal Structure Determination

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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

Abstract

Keywords

ASJC Scopus subject areas

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Datasets

CCDC 856042: Experimental Crystal Structure Determination

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