Cobalt-Catalyzed Asymmetric 1,4-Reduction of α,β-Unsaturated Nitriles with HBpin

A series of novel AAO ligands were synthesized and employed in the cobalt-catalyzed asymmetric 1,4-reduction of α,β-unsaturated nitriles with HBpin, affording β-stereogenic alkyl nitriles with high enantioselectivities. This protocol can be scaled to gram quantities with a low catalyst loading (0.5 mol %) and demonstrates broad synthetic utility, as evidenced by the efficient transformation of the enantioenriched products into valuable chiral building blocks, including aldehydes, carboxylic acids, amides, and ketones.

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Publication Details

Journal
Organic Letters
Published
2025-11-20
DOI
https://doi.org/10.1021/acs.orglett.5c04453
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Cobalt-Catalyzed Asymmetric 1,4-Reduction of α,β-Unsaturated Nitriles with HBpin

Cheng‐Gong Zheng, Li Ma, Qing Xu, Yuanzhi Xia et al.
Organic Letters
Catalytic C–H Functionalization Methods
article

Cobalt-Catalyzed Asymmetric 1,4-Reduction of α,β-Unsaturated Nitriles with HBpin

Cheng‐Gong Zheng, Li Ma, Qing Xu, Yuanzhi Xia, Zhaolin Wang, J. Tang, Yifei Chen, Jianhui Chen, Yanshu Luo, Jialong Xv, Biao Cheng
article en

Abstract

A series of novel AAO ligands were synthesized and employed in the cobalt-catalyzed asymmetric 1,4-reduction of α,β-unsaturated nitriles with HBpin, affording β-stereogenic alkyl nitriles with high enantioselectivities. This protocol can be scaled to gram quantities with a low catalyst loading (0.5 mol %) and demonstrates broad synthetic utility, as evidenced by the efficient transformation of the enantioenriched products into valuable chiral building blocks, including aldehydes, carboxylic acids, amides, and ketones.

Organic LettersVol. 27(48)
Wenzhou University (CN), Tobacco Research Institute (CN), Division of Materials Science and Engineering (AU), Henan Agricultural University (CN), Zhejiang University (CN)
Openalex Percentile: Top 73%
Catalytic C–H Functionalization Methods
DOISourceOpenAlex
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Cobalt-Catalyzed Asymmetric 1,4-Reduction of α,β-Unsaturated Nitriles with HBpin — Cheng‐Gong Zheng, Li Ma, et al. · Organic Letters (2025) | TGRS Research Map | TGRS