ArticleACS catalysis2021
Enantioselective Inverse-Electron Demand Aza-Diels-Alder Reaction: ipso,α-Selectivity of Silyl Dienol Ethers.
Article in ACS catalysis, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Transition-metal-free regioselective synthesis of spiro-oxazolidines through [3 + 2] annulation reactions of azadienes with haloalcohols.RSC advances · 2025Article
- Bicarbonate-binding catalysis for the enantioselective desymmetrization of keto sulfonium salts.Nature communications · 2024Article
- Non-covalent organocatalyzed enantioselective cyclization reactions of α,β-unsaturated imines.Beilstein journal of organic chemistry · 2024Review
- A Lewis Acid-Promoted Michael Addition and Ring-Expansion Cascade for the Construction of Nitrogen-Containing Medium-Sized Rings.Molecules (Basel, Switzerland) · 2023Article
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Authors and funding
5 authors.
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Abstract
A highly efficient enantioselective inverse-electron-demand aza-Diels-Alder reaction between aza-sulfonyl-1-aza-1,3-butadienes and silyl (di)enol ethers has been developed. The presented methodology allows the synthesis of benzofuran-fused 2-piperidinol derivatives with three contiguous stereocenters in a highly selective manner, as even the hemiaminal center is completely stereocontrolled. Density functional theory (DFT) calculations support that the hydrogen-bond donor-based bifunctional organocatalyst selectively triggers the reaction through the ipso,α-position of the dienophile, in contrast to the reactivity observed for dienolates in situ generated from β,γ-unsaturated derivatives. Moreover, the calculations have clarified the mechanism of the reaction and the ability of the hydrogen-bond donor core to hydrolyze selectively the
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