Stereoselective Route to 2,3,4,5-Tetraaryltetrahydrofurans via Efficient Cascade Synthesis of 2,3-Dihydrofurans with Four Different (Hetero)Aryl Substituents

Haoran Wang; Sunewang R. Wang

doi:10.1021/acs.orglett.5c00450

Stereoselective Route to 2,3,4,5-Tetraaryltetrahydrofurans via Efficient Cascade Synthesis of 2,3-Dihydrofurans with Four Different (Hetero)Aryl Substituents

Haoran Wang
, Sunewang R. Wang^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

Abstract

Tf₂NH-mediated regio- and diastereoselective skeletal metamorphosis of 1-alkynyl-2,3-diaryl-2-methoxycarbonylcyclopropyl ketones readily gave 2,3,4,5-tetraaryl-2,3-dihydrofurans. Controllable reduction and removal of the ester group then precisely afforded four types of the eight possible tetrahydrofuran (THF) diastereomers with four different (hetero)aryl substituents. Further, deuterium-labeling results revealed an unprecedented hydrogen transfer from the formyl C-H bond in ^tBuOK-promoted decarbonylation under ^tBuOH-free conditions.

Original language	English
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.5c00450
State	Accepted/In press - 2025

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@article{d4fb5f5b2f354fdd8a1b4600c5f97c91,

title = "Stereoselective Route to 2,3,4,5-Tetraaryltetrahydrofurans via Efficient Cascade Synthesis of 2,3-Dihydrofurans with Four Different (Hetero)Aryl Substituents",

abstract = "Tf2NH-mediated regio- and diastereoselective skeletal metamorphosis of 1-alkynyl-2,3-diaryl-2-methoxycarbonylcyclopropyl ketones readily gave 2,3,4,5-tetraaryl-2,3-dihydrofurans. Controllable reduction and removal of the ester group then precisely afforded four types of the eight possible tetrahydrofuran (THF) diastereomers with four different (hetero)aryl substituents. Further, deuterium-labeling results revealed an unprecedented hydrogen transfer from the formyl C-H bond in tBuOK-promoted decarbonylation under tBuOH-free conditions.",

author = "Haoran Wang and Wang, \{Sunewang R.\}",

note = "Publisher Copyright: {\textcopyright} 2025 American Chemical Society.",

year = "2025",

doi = "10.1021/acs.orglett.5c00450",

language = "英语",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Stereoselective Route to 2,3,4,5-Tetraaryltetrahydrofurans via Efficient Cascade Synthesis of 2,3-Dihydrofurans with Four Different (Hetero)Aryl Substituents

AU - Wang, Haoran

AU - Wang, Sunewang R.

PY - 2025

Y1 - 2025

N2 - Tf2NH-mediated regio- and diastereoselective skeletal metamorphosis of 1-alkynyl-2,3-diaryl-2-methoxycarbonylcyclopropyl ketones readily gave 2,3,4,5-tetraaryl-2,3-dihydrofurans. Controllable reduction and removal of the ester group then precisely afforded four types of the eight possible tetrahydrofuran (THF) diastereomers with four different (hetero)aryl substituents. Further, deuterium-labeling results revealed an unprecedented hydrogen transfer from the formyl C-H bond in tBuOK-promoted decarbonylation under tBuOH-free conditions.

AB - Tf2NH-mediated regio- and diastereoselective skeletal metamorphosis of 1-alkynyl-2,3-diaryl-2-methoxycarbonylcyclopropyl ketones readily gave 2,3,4,5-tetraaryl-2,3-dihydrofurans. Controllable reduction and removal of the ester group then precisely afforded four types of the eight possible tetrahydrofuran (THF) diastereomers with four different (hetero)aryl substituents. Further, deuterium-labeling results revealed an unprecedented hydrogen transfer from the formyl C-H bond in tBuOK-promoted decarbonylation under tBuOH-free conditions.

UR - https://www.scopus.com/pages/publications/105000727738

U2 - 10.1021/acs.orglett.5c00450

DO - 10.1021/acs.orglett.5c00450

M3 - 文章

AN - SCOPUS:105000727738

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

Stereoselective Route to 2,3,4,5-Tetraaryltetrahydrofurans via Efficient Cascade Synthesis of 2,3-Dihydrofurans with Four Different (Hetero)Aryl Substituents

Abstract

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