Nickel-Catalyzed Dynamic Kinetic Asymmetric Reductive Arylation of Aldehydes with Heterobiaryl Triflates

In this context, we report a nickel-catalyzed dynamic kinetic asymmetric reductive arylation of aldehydes with racemic heterobiaryl triflates, offering a series of axially chiral heterobiaryls bearing a centrally chiral secondary alcohol moiety in a highly diastereo- and enantioselective manner. The simultaneous control of both axial and central stereogenic elements of the products lies in the stereoselective nucleophilic addition of the configurationally labile hetereobiaryl nickel complex to the formyl group of aldehydes.

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Publication Details

Journal
Organic Letters
Published
2025-03-15
DOI
https://doi.org/10.1021/acs.orglett.5c00441
Citations
13
Primary Topic
Axial and Atropisomeric Chirality Synthesis
Type
article
Field-Weighted Citation Impact
12.17

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article

Nickel-Catalyzed Dynamic Kinetic Asymmetric Reductive Arylation of Aldehydes with Heterobiaryl Triflates

Chuan Wang, Xinran Ding
13 citations
Organic Letters
Axial and Atropisomeric Chirality Synthesis
12.17
article

Nickel-Catalyzed Dynamic Kinetic Asymmetric Reductive Arylation of Aldehydes with Heterobiaryl Triflates

Chuan Wang, Xinran Ding
article en
13 citations

Abstract

In this context, we report a nickel-catalyzed dynamic kinetic asymmetric reductive arylation of aldehydes with racemic heterobiaryl triflates, offering a series of axially chiral heterobiaryls bearing a centrally chiral secondary alcohol moiety in a highly diastereo- and enantioselective manner. The simultaneous control of both axial and central stereogenic elements of the products lies in the stereoselective nucleophilic addition of the configurationally labile hetereobiaryl nickel complex to the formyl group of aldehydes.

Organic LettersVol. 27(12)
University of Science and Technology of China (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 1%
Axial and Atropisomeric Chirality Synthesis
12.17
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