Construction of tetrahydrofuran-3-ones from readily available organochalcogen precursors via radical carbonylation/reductive cyclization.

Construction of tetrahydrofuran-3-ones from readily available organochalcogen precursors via radical carbonylation/reductive cyclization.
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DOI:
10.1021/ol016127q
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发表时间:
2002-01
期刊:
影响因子:
5.2
通讯作者:
S. Berlin;C. Ericsson;L. Engman
S. Berlin;C. Ericsson;L. Engman
中科院分区:
化学1区
文献类型:
--
作者:
S. Berlin;C. Ericsson;L. Engman

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[reaction: see text] beta-Hydroxyalkyl aryl chalcogenides, readily available by regioselective ring-opening of epoxides with nucleophilic benzeneselenolate or tellurolate, were O-alkylated by treatment with ethyl propiolate or (E)-1,2-bis(phenylsulfonyl)ethylene. Subsequent carbonylation/reductive cyclization in the presence of AIBN/TTMSS and carbon monoxide (80 atm) afforded tetrahydrofuran-3-ones in moderate to good yields.