Catalytic Asymmetric Oxidative γ-Coupling of α,β-Unsaturated Aldehydes with Air as the Terminal Oxidant

Line Næsborg; Vasco Corti; Lars Astrup Leth; Pernille H. Poulsen; Karl Anker Jørgensen

doi:10.1002/anie.201711944

Catalytic Asymmetric Oxidative γ-Coupling of α,β-Unsaturated Aldehydes with Air as the Terminal Oxidant

Line Næsborg, Vasco Corti, Lars Astrup Leth, Pernille H. Poulsen, Karl Anker Jørgensen^*

^*Corresponding author for this work

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

Abstract

A novel concept for catalytic asymmetric coupling reactions is presented. Merging organocatalysis with single-electron oxidation by using a catalytic amount of a copper(II) salt and air as the terminal oxidant, we have developed a highly stereoselective carbon–carbon oxidative coupling reaction of α,β-unsaturated aldehydes. The concept relies on the generation of a dienamine intermediate, which is oxidized to an open-shell activated species that undergoes highly selective γ-homo- and γ-heterocoupling reactions. In the majority of examples presented, only a single stereoisomer was formed.

Original language	English
Journal	Angewandte Chemie - International Edition
Volume	57
Issue	6
Pages (from-to)	1606-1610
Number of pages	5
ISSN	1433-7851
DOIs	https://doi.org/10.1002/anie.201711944
Publication status	Published - 5 Feb 2018

Keywords

asymmetric catalysis
organocatalysis
oxidative coupling
single-electron transfer
synthetic methods

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10.1002/anie.201711944

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title = "Catalytic Asymmetric Oxidative γ-Coupling of α,β-Unsaturated Aldehydes with Air as the Terminal Oxidant",

abstract = "A novel concept for catalytic asymmetric coupling reactions is presented. Merging organocatalysis with single-electron oxidation by using a catalytic amount of a copper(II) salt and air as the terminal oxidant, we have developed a highly stereoselective carbon–carbon oxidative coupling reaction of α,β-unsaturated aldehydes. The concept relies on the generation of a dienamine intermediate, which is oxidized to an open-shell activated species that undergoes highly selective γ-homo- and γ-heterocoupling reactions. In the majority of examples presented, only a single stereoisomer was formed.",

keywords = "asymmetric catalysis, organocatalysis, oxidative coupling, single-electron transfer, synthetic methods",

author = "Line N{\ae}sborg and Vasco Corti and Leth, {Lars Astrup} and Poulsen, {Pernille H.} and J{\o}rgensen, {Karl Anker}",

year = "2018",

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doi = "10.1002/anie.201711944",

language = "English",

volume = "57",

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journal = "Angewandte Chemie - International Edition",

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Catalytic Asymmetric Oxidative γ-Coupling of α,β-Unsaturated Aldehydes with Air as the Terminal Oxidant. / Næsborg, Line; Corti, Vasco; Leth, Lars Astrup et al.
In: Angewandte Chemie - International Edition, Vol. 57, No. 6, 05.02.2018, p. 1606-1610.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

TY - JOUR

T1 - Catalytic Asymmetric Oxidative γ-Coupling of α,β-Unsaturated Aldehydes with Air as the Terminal Oxidant

AU - Næsborg, Line

AU - Corti, Vasco

AU - Leth, Lars Astrup

AU - Poulsen, Pernille H.

AU - Jørgensen, Karl Anker

PY - 2018/2/5

Y1 - 2018/2/5

N2 - A novel concept for catalytic asymmetric coupling reactions is presented. Merging organocatalysis with single-electron oxidation by using a catalytic amount of a copper(II) salt and air as the terminal oxidant, we have developed a highly stereoselective carbon–carbon oxidative coupling reaction of α,β-unsaturated aldehydes. The concept relies on the generation of a dienamine intermediate, which is oxidized to an open-shell activated species that undergoes highly selective γ-homo- and γ-heterocoupling reactions. In the majority of examples presented, only a single stereoisomer was formed.

AB - A novel concept for catalytic asymmetric coupling reactions is presented. Merging organocatalysis with single-electron oxidation by using a catalytic amount of a copper(II) salt and air as the terminal oxidant, we have developed a highly stereoselective carbon–carbon oxidative coupling reaction of α,β-unsaturated aldehydes. The concept relies on the generation of a dienamine intermediate, which is oxidized to an open-shell activated species that undergoes highly selective γ-homo- and γ-heterocoupling reactions. In the majority of examples presented, only a single stereoisomer was formed.

KW - asymmetric catalysis

KW - organocatalysis

KW - oxidative coupling

KW - single-electron transfer

KW - synthetic methods

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DO - 10.1002/anie.201711944

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C2 - 29265675

AN - SCOPUS:85040684268

SN - 1433-7851

VL - 57

SP - 1606

EP - 1610

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 6

ER -

Catalytic Asymmetric Oxidative γ-Coupling of α,β-Unsaturated Aldehydes with Air as the Terminal Oxidant

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Keywords

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