Enantioselective Cross-Coupling of Electron-Deficient Alkenes via Ir-Catalyzed Vinylic sp2C-H Alkylation

Takanori Shibata; Masafumi Kojima; Sahoko Onoda; Mamoru Ito

doi:10.1021/acs.orglett.1c02823

Enantioselective Cross-Coupling of Electron-Deficient Alkenes via Ir-Catalyzed Vinylic sp²C-H Alkylation

Takanori Shibata^*, Masafumi Kojima, Sahoko Onoda, Mamoru Ito

^*Corresponding author for this work

School of Advanced Science and Engineering

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

11 Citations (Scopus)

Abstract

A chiral Ir-catalyzed reaction of α-aryl-α,β-unsaturated amides with β-substituted acrylates proceeded to give formal conjugate adducts in high yield and ee (up to 99% yield and up to 95% ee). This is the first example of the enantioselective cross-coupling of two different electron-deficient alkenes via vinylic sp2 C-H activation, and polyfunctionalized chiral compounds were obtained.

Original language	English
Pages (from-to)	8158-8162
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.1c02823
Publication status	Published - 2021 Nov 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c02823

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abstract = "A chiral Ir-catalyzed reaction of α-aryl-α,β-unsaturated amides with β-substituted acrylates proceeded to give formal conjugate adducts in high yield and ee (up to 99% yield and up to 95% ee). This is the first example of the enantioselective cross-coupling of two different electron-deficient alkenes via vinylic sp2 C-H activation, and polyfunctionalized chiral compounds were obtained. ",

author = "Takanori Shibata and Masafumi Kojima and Sahoko Onoda and Mamoru Ito",

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AU - Shibata, Takanori

AU - Kojima, Masafumi

AU - Onoda, Sahoko

AU - Ito, Mamoru

N1 - Funding Information: This work was supported by Waseda University Grant for Special Research Projects. Publisher Copyright: ©

PY - 2021/11/5

Y1 - 2021/11/5

N2 - A chiral Ir-catalyzed reaction of α-aryl-α,β-unsaturated amides with β-substituted acrylates proceeded to give formal conjugate adducts in high yield and ee (up to 99% yield and up to 95% ee). This is the first example of the enantioselective cross-coupling of two different electron-deficient alkenes via vinylic sp2 C-H activation, and polyfunctionalized chiral compounds were obtained.

AB - A chiral Ir-catalyzed reaction of α-aryl-α,β-unsaturated amides with β-substituted acrylates proceeded to give formal conjugate adducts in high yield and ee (up to 99% yield and up to 95% ee). This is the first example of the enantioselective cross-coupling of two different electron-deficient alkenes via vinylic sp2 C-H activation, and polyfunctionalized chiral compounds were obtained.

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JO - Organic Letters

JF - Organic Letters

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ER -

Enantioselective Cross-Coupling of Electron-Deficient Alkenes via Ir-Catalyzed Vinylic sp²C-H Alkylation

Abstract

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