General [4 + 1] Cyclization Approach To Access 2,2-Disubstituted Tetrahydrofurans Enabled by Electrophilic Bifunctional Peroxides

General [4 + 1] Cyclization Approach To Access 2,2-Disubstituted Tetrahydrofurans Enabled by Electrophilic Bifunctional Peroxides

A general [4 + 1] cyclization reaction of carbonyl nucleophiles with 2-iodomethylallyl peroxides, which function as unique electrophilic oxygen synthons, for the synthesis of a broad range of 2,2-disubstituted tetrahydrofurans is achieved under operationally simple conditions. The unprecedented asym...

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Veröffentlicht in:Organic letters 2019-07, Vol.21 (14), p.5679-5684
Hauptverfasser: Gao, Min, Zhao, Yukun, Zhong, Chen, Liu, Shengshu, Liu, Pengkang, Yin, Qi, Hu, Lin
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container_end_page 5684
container_issue 14
container_start_page 5679
container_title Organic letters
container_volume 21
creator Gao, Min
Zhao, Yukun
Zhong, Chen
Liu, Shengshu
Liu, Pengkang
Yin, Qi
Hu, Lin
description A general [4 + 1] cyclization reaction of carbonyl nucleophiles with 2-iodomethylallyl peroxides, which function as unique electrophilic oxygen synthons, for the synthesis of a broad range of 2,2-disubstituted tetrahydrofurans is achieved under operationally simple conditions. The unprecedented asymmetric version of such reaction is also realized via chiral auxiliary-assisted cyclization, thus providing a distinct approach to access chiral tetrahydrofurans with high diastereoselectivities. The new method can be applied to the synthesis of core structure of posaconazole drug.
doi_str_mv 10.1021/acs.orglett.9b02012
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title General [4 + 1] Cyclization Approach To Access 2,2-Disubstituted Tetrahydrofurans Enabled by Electrophilic Bifunctional Peroxides
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