Palladium-CatalyzedDivergent Synthesis from <i>o</i>‑Sulfonamido Trifluoroacetophenonesand 2‑En-4-ynylCarbonates

Here we present a palladium-catalyzed divergent transformative reaction between <i>o-</i>sulfonamido trifluoroacetophenones and 2-en-4-ynyl carbonates. A spectrum of enantioenriched 2,5-dihydrofuran-fused tetrahydroquinolines bearing either a (<i>Z</i>)- or (<i>E</i>)-exocyclic double bond are constructed with moderate to high enantioselectivity from 5-aryl-substituted carbonates by tuning palladium sources, while analogous 2,3-dihydrofuran-fused products are furnished by using 5-alkyl-substituted ones.

Publication Details

Journal
Figshare
Published
2025-02-15
DOI
https://doi.org/10.1021/acs.orglett.5c00269.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Palladium-CatalyzedDivergent Synthesis from o‑Sulfonamido Trifluoroacetophenonesand 2‑En-4-ynylCarbonates

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Catalytic C–H Functionalization Methods
article

Palladium-CatalyzedDivergent Synthesis from o‑Sulfonamido Trifluoroacetophenonesand 2‑En-4-ynylCarbonates

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Abstract

Here we present a palladium-catalyzed divergent transformative reaction between <i>o-</i>sulfonamido trifluoroacetophenones and 2-en-4-ynyl carbonates. A spectrum of enantioenriched 2,5-dihydrofuran-fused tetrahydroquinolines bearing either a (<i>Z</i>)- or (<i>E</i>)-exocyclic double bond are constructed with moderate to high enantioselectivity from 5-aryl-substituted carbonates by tuning palladium sources, while analogous 2,3-dihydrofuran-fused products are furnished by using 5-alkyl-substituted ones.

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Catalytic C–H Functionalization Methods
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Palladium-CatalyzedDivergent Synthesis from <i>o</i>‑Sulfonamido Trifluoroacetophenonesand 2‑En-4-ynylCarbonates · Figshare (2025) | TGRS Research Map | TGRS