Atroposelective catalysis

Schmidt, Tanno A.; Hutskalova, Valeriia; Sparr, Christof

doi:10.1038/s41570-024-00618-x

Nat Rev Chem

2024

DOI: 10.1038/s41570-024-00618-x

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Atroposelective catalysis

Tanno A. Schmidt,

Valeriia Hutskalova,

Christof Sparr

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2024

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Cited by 4 publications

References 357 publications

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Atroposelective Arene‐Forming Wittig Reaction by Phosphorus P^III/P^V=O Redox Catalysis

Jana,

Zhao,

Musies

et al. 2024

Angewandte Chemie

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The Wittig reaction is renowned as exceptionally versatile method for converting a diversity of aldehydes and ketones into alkenes. Recently, strategies for chiral phosphine catalysis under PIII/PV=O redox cycling emerged to render this venerable transformation stereoselective. Herein, we describe that phosphine redox catalysis enables the enantioselective synthesis of pertinent biaryl atropisomers by means of a stereocontrolled arene‐forming Wittig reaction. Key to the process is the release of an endogenous base from readily accessible tert‐butyloxycarbonylated Morita–Baylis–Hillman adducts triggered by catalyst intramolecularization, permitting mild phosphine redox catalysis for atroposelective Wittig reactions. By this strategy, a broad diversity of biaryl atropisomers is obtained with up to 94:6 enantioselectivity.

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Atroposelective Arene‐Forming Wittig Reaction by Phosphorus P^III/P^V=O Redox Catalysis

Jana,

Zhao,

Musies

et al. 2024

Angewandte Chemie

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Atroposelective Arene‐Forming Wittig Reaction by Phosphorus P^III/P^V=O Redox Catalysis

Jana,

Zhao,

Musies

et al. 2024

Angew Chem Int Ed

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Asymmetric electrophilic functionalization of amino-substituted heteroaromatic compounds: a convenient tool for the enantioselective synthesis of nitrogen heterocycles

Blay,

Monleón,

Montesinos-Magraner

et al. 2024

Chem. Commun.

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Atroposelective catalysis

Cited by 4 publications

References 357 publications

Atroposelective Arene‐Forming Wittig Reaction by Phosphorus P^III/P^V=O Redox Catalysis

Atroposelective Arene‐Forming Wittig Reaction by Phosphorus P^III/P^V=O Redox Catalysis

Atroposelective Arene‐Forming Wittig Reaction by Phosphorus P^III/P^V=O Redox Catalysis

Asymmetric electrophilic functionalization of amino-substituted heteroaromatic compounds: a convenient tool for the enantioselective synthesis of nitrogen heterocycles

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Atroposelective catalysis

Cited by 4 publications

References 357 publications

Atroposelective Arene‐Forming Wittig Reaction by Phosphorus PIII/PV=O Redox Catalysis

Atroposelective Arene‐Forming Wittig Reaction by Phosphorus PIII/PV=O Redox Catalysis

Atroposelective Arene‐Forming Wittig Reaction by Phosphorus PIII/PV=O Redox Catalysis

Asymmetric electrophilic functionalization of amino-substituted heteroaromatic compounds: a convenient tool for the enantioselective synthesis of nitrogen heterocycles

Contact Info

Product

Resources

About

Atroposelective Arene‐Forming Wittig Reaction by Phosphorus P^III/P^V=O Redox Catalysis

Atroposelective Arene‐Forming Wittig Reaction by Phosphorus P^III/P^V=O Redox Catalysis

Atroposelective Arene‐Forming Wittig Reaction by Phosphorus P^III/P^V=O Redox Catalysis