Rh(I)/Sulfoxide‐Imine‐Olefin Complex Catalyzed Enantioselective Allylic Alkylation of 2‐Fluoromalonate: Synthesis of Chiral α‐Fluorolactone Bearing Vicinal Stereogenic Centers

Highly enantioselective Rh-catalyzed allylic substitution of the racemic branched allylic substrates with 2-fluoromalonate was realized enabled by a novel chiral sulfoxide-imine-olefin ligand under mild reaction conditions. The utilization of CuSO<sub>4</sub> is beneficial for improving the enantioselectivity. Notably, the chiral fluoro-containing allyl products can be employed in a selective cyclic esterification to form chiral α-fluorolactone bearing vicinal stereogenic centers.

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Publication Details

Journal
Chemistry - A European Journal
Published
2024-08-16
DOI
https://doi.org/10.1002/chem.202402875
Citations
1
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
0.16

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article

Rh(I)/Sulfoxide‐Imine‐Olefin Complex Catalyzed Enantioselective Allylic Alkylation of 2‐Fluoromalonate: Synthesis of Chiral α‐Fluorolactone Bearing Vicinal Stereogenic Centers

Hongbo Zhang, Haibin Jiang, Wenwen Zhao, Sheng‐Cai Zheng et al.
1 citations
Chemistry - A European Journal
Asymmetric Hydrogenation and Catalysis
0.16
article

Rh(I)/Sulfoxide‐Imine‐Olefin Complex Catalyzed Enantioselective Allylic Alkylation of 2‐Fluoromalonate: Synthesis of Chiral α‐Fluorolactone Bearing Vicinal Stereogenic Centers

Hongbo Zhang, Haibin Jiang, Wenwen Zhao, Sheng‐Cai Zheng, Xiaolin Wang, Xiao-Ming Zhao
article en
1 citations

Abstract

Highly enantioselective Rh-catalyzed allylic substitution of the racemic branched allylic substrates with 2-fluoromalonate was realized enabled by a novel chiral sulfoxide-imine-olefin ligand under mild reaction conditions. The utilization of CuSO<sub>4</sub> is beneficial for improving the enantioselectivity. Notably, the chiral fluoro-containing allyl products can be employed in a selective cyclic esterification to form chiral α-fluorolactone bearing vicinal stereogenic centers.

Chemistry - A European JournalVol. 30(68)
Tongji University (CN)
National Natural Science Foundation of China, Fundamental Research Funds for the Central Universities
Clean water and sanitation
Openalex Percentile: Top 59%
Asymmetric Hydrogenation and Catalysis
0.16
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Rh(I)/Sulfoxide‐Imine‐Olefin Complex Catalyzed Enantioselective Allylic Alkylation of 2‐Fluoromalonate: Synthesis of Chiral α‐Fluorolactone Bearing Vicinal Stereogenic Centers — Hongbo Zhang, Haibin Jiang, et al. · Chemistry - A European Journal (2024) | TGRS Research Map | TGRS