Intramolecular cyclization of 1-nitroalkenyl radicals generated by one-electron oxidation of aci-nitro anions with CAN: stereoselective formation of 3,4-functionalized tetrahydrofurans
Intramolecular cyclization of 1-nitroalkenyl radicals generated by one-electron oxidation of aci-nitro anions with CAN: stereoselective formation of 3,4-functionalized tetrahydrofurans
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CAN通过单电子氧化酰基硝基阴离子产生的1-硝基烯基自由基的分子内环化：立体选择性形成3,4-官能化四氢呋喃
DOI：
10.1039/a907842h
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发表时间：
1999
影响因子：
4.9
通讯作者：
J. Dulcere
中科院分区：
文献类型：
--
作者：
A. Durand;E. Dumez;Jean Rodriguez;J. Dulcere
在六硝酸辛酸铵（IV）（CAN）的单电子氧化作用下，烯丙醇与α，β-二取代硝基烯烃1a-d的氧杂-迈克尔加成反应产生的酸-硝基阴离子3a-d进行立体选择性自由基环化，生成3-硝基-4-硝基氧甲基四氢呋喃6a-d和3-硝基-4-羟甲基四氢呋喃7，8a-d。
Upon one-electron oxidation by ammonium hexanitratocerate(IV) (CAN), aci-nitro anions 3a-d resulting from oxa-Michael addition of allylic alcohol to α,β-disubstituted nitroalkenes 1a-d undergo stereoselective radical cyclization into 3-nitro-4-nitrooxymethyltetrahydrofurans 6a-d and 3-nitro-4-hydroxymethyltetrahydrofurans 7,8a-d.