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 CuSO4 is beneficial for improving the enantioselectivity....

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Published in:Chemistry : a European journal 2024-12, Vol.30 (68), p.e202402875-n/a
Main Authors: Jiang, Haibin, Zhao, Wen‐Wen, Wang, Xiaolin, Zhang, Hongbo, Zheng, Sheng‐Cai, Zhao, Xiaoming
Format: Article
Language:English
Subjects:
Alkylation
Allylic substitution
Chemical synthesis
Chiral carbon-fluorine center
Enantiomers
Esterification
Fluorolactone
Substitution reactions
Sulfoxide ligand
Sulfoxides
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container_start_page e202402875
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creator Jiang, Haibin
Zhao, Wen‐Wen
Wang, Xiaolin
Zhang, Hongbo
Zheng, Sheng‐Cai
Zhao, Xiaoming
description 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 CuSO4 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. Chiral fluorolactones A novel chiral sulfoxide‐imine‐olefin ligand is applyed to a rhodium catalyzed allylic substitution with monofluoro building block, resulting in high regio‐ and enantioselective fluorine containing allylic compounds which can be transferred to chiral fluorinated δ‐lactones bearing vicinal stereogenic centers.
doi_str_mv 10.1002/chem.202402875
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subjects Alkylation
Allylic substitution
Chemical synthesis
Chiral carbon-fluorine center
Enantiomers
Esterification
Fluorolactone
Substitution reactions
Sulfoxide ligand
Sulfoxides
title Rh(I)/Sulfoxide‐Imine‐Olefin Complex Catalyzed Enantioselective Allylic Alkylation of 2‐Fluoromalonate: Synthesis of Chiral α‐Fluorolactone Bearing Vicinal Stereogenic Centers
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