Nickel-CatalyzedOne-Pot H/D Exchange and AsymmetricMichael Addition in the Presence of D<sub>2</sub>O

A step-economical and efficient strategy for the enantioselective synthesis of tetradeuterated γ-nitroketones using a cost-effective and readily available deuterium source is highly desirable. Herein, we report a nickel-catalyzed one-pot H/D exchange and highly enantioselective Michael addition of α,β-unsaturated 2-acyl imidazoles with nitromethane in the presence of D<sub>2</sub>O. This protocol demonstrates excellent efficiency, high enantioselectivity, and a broad substrate scope, offering a practical and versatile approach to accessing deuterium-labeled compounds.

Publication Details

Journal
Figshare
Published
2025-03-24
DOI
https://doi.org/10.1021/acs.joc.4c02860.s002
Primary Topic
Chemical Reactions and Isotopes
Type
article
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article

Nickel-CatalyzedOne-Pot H/D Exchange and AsymmetricMichael Addition in the Presence of D2O

Figshare
Chemical Reactions and Isotopes
article

Nickel-CatalyzedOne-Pot H/D Exchange and AsymmetricMichael Addition in the Presence of D2O

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Abstract

A step-economical and efficient strategy for the enantioselective synthesis of tetradeuterated γ-nitroketones using a cost-effective and readily available deuterium source is highly desirable. Herein, we report a nickel-catalyzed one-pot H/D exchange and highly enantioselective Michael addition of α,β-unsaturated 2-acyl imidazoles with nitromethane in the presence of D<sub>2</sub>O. This protocol demonstrates excellent efficiency, high enantioselectivity, and a broad substrate scope, offering a practical and versatile approach to accessing deuterium-labeled compounds.

Figshare
Openalex Percentile: Top 65%
Chemical Reactions and Isotopes
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Nickel-CatalyzedOne-Pot H/D Exchange and AsymmetricMichael Addition in the Presence of D<sub>2</sub>O · Figshare (2025) | TGRS Research Map | TGRS