Organocatalytic Enantioselective Vinylogous Allylic Alkylation between β,γ‐Unsaturated Pyrazoleamides and MBH Carbonates

Abstract The direct asymmetric vinylogous allylic alkylation is an efficient method to construct chiral 1,5‐diene compounds. In this work, acyclic unsaturated amides are used as a nucleophile for enantioselective vinylogous allylic alkylation. With 10 mol % of chiral tertiary amine C11 , the enantioselective vinylogous allylic alkylation between β,γ‐unsaturated pyrazoleamides and Morita‐Baylis‐Hillman carbonates is achieved, affording optically active multifunctional chiral 1,5‐dienes in moderate‐to‐excellent yields (74–99 %) with good‐to‐excellent enantioselectivities (67–94 % ee).

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2024-10-14
DOI
https://doi.org/10.1002/ejoc.202400799
Citations
1
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
0.25
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article

Organocatalytic Enantioselective Vinylogous Allylic Alkylation between β,γ‐Unsaturated Pyrazoleamides and MBH Carbonates

Jun‐Hao Fu, Xin‐Yan Wu, Feng Sha, Yunpeng He
1 citations
European Journal of Organic Chemistry
Asymmetric Synthesis and Catalysis
0.25
article

Organocatalytic Enantioselective Vinylogous Allylic Alkylation between β,γ‐Unsaturated Pyrazoleamides and MBH Carbonates

Jun‐Hao Fu, Xin‐Yan Wu, Feng Sha, Yunpeng He
article en
1 citations

Abstract

Abstract The direct asymmetric vinylogous allylic alkylation is an efficient method to construct chiral 1,5‐diene compounds. In this work, acyclic unsaturated amides are used as a nucleophile for enantioselective vinylogous allylic alkylation. With 10 mol % of chiral tertiary amine C11 , the enantioselective vinylogous allylic alkylation between β,γ‐unsaturated pyrazoleamides and Morita‐Baylis‐Hillman carbonates is achieved, affording optically active multifunctional chiral 1,5‐dienes in moderate‐to‐excellent yields (74–99 %) with good‐to‐excellent enantioselectivities (67–94 % ee).

European Journal of Organic ChemistryVol. 27(46)
East China University of Science and Technology (CN)
Openalex Percentile: Top 48%
Asymmetric Synthesis and Catalysis
0.25
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Organocatalytic Enantioselective Vinylogous Allylic Alkylation between β,γ‐Unsaturated Pyrazoleamides and MBH Carbonates — Jun‐Hao Fu, Xin‐Yan Wu, et al. · European Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS