Stereocontrolled Synthesis of Aryl C‑Nucleosides under Ambient Conditions

Stereocontrolled Synthesis of Aryl C‑Nucleosides under Ambient Conditions

A stereocontrolled synthesis of an aryl C-nucleoside has been developed using D-ribals and arylboronic acids catalyzed by palladium without additional ligands in common solvents under an open-air atmosphere at room temperature. This protocol features very mild conditions, simplicity in operation, ex...

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Veröffentlicht in:Organic letters 2024-06, Vol.26 (24), p.5162-5166
Hauptverfasser: Xie, Rui, Xu, Jing, Shi, Haolin, Xiao, Chenyu, Wang, Nengzhong, Huang, Nianyu, Yao, Hui
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Sprache:eng
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ambient temperature
glycosylation
ligands
palladium
stereoselective synthesis
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container_end_page 5166
container_issue 24
container_start_page 5162
container_title Organic letters
container_volume 26
creator Xie, Rui
Xu, Jing
Shi, Haolin
Xiao, Chenyu
Wang, Nengzhong
Huang, Nianyu
Yao, Hui
description A stereocontrolled synthesis of an aryl C-nucleoside has been developed using D-ribals and arylboronic acids catalyzed by palladium without additional ligands in common solvents under an open-air atmosphere at room temperature. This protocol features very mild conditions, simplicity in operation, exclusive β-stereoselectivity, broad substrate scopes, and good compatibility with reactive amino and hydroxyl groups. The functionalization of unsaturated C-nucleosides and the late-stage glycosylation of natural products/drugs demonstrated the high practicality of this strategy.
doi_str_mv 10.1021/acs.orglett.4c01664
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source American Chemical Society Journals
subjects ambient temperature
glycosylation
ligands
palladium
stereoselective synthesis
title Stereocontrolled Synthesis of Aryl C‑Nucleosides under Ambient Conditions
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