Diastereoselective building up polycyclic tetrahydrofurans via tandem annulation of 1,n-enynes with aliphatic acids,Organic Chemistry Frontiers

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Diastereoselective building up polycyclic tetrahydrofurans via tandem annulation of 1,n-enynes with aliphatic acids
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2017-07-24 00:00:00 , DOI: 10.1039/c7qo00527j
Leiyang Lv _{1,

2,

3,

4,

5} , Shenglin Lu _{1,

2,

3,

4} , Yuanjin Chen _{1,

2,

3,

4} , Zhiping Li _{1,

2,

3,

4}

Affiliation

A silver-catalyzed tandem annulation of aniline-linked 1,7-enynes with aliphatic acids has been reported. This synergistic tandem annulations allow the straightforward and efficient building up various highly diastereoselective polycyclic tetrahydrofurans. Primary and secondary acids undergo decarboxylation/cascade radical addition/α-C(sp³)–H cleavage/cycloalkylation/O-trapping to generate oxygenous [6.6.6.5] fused products. While tertiary acids undergo decarboxylation/cascade radcial addition/β-C(sp³)–H cleavage/O-trapping to give oxygenous [6.6.6.6] fused products.

中文翻译：

非对映选择性通过1，n-炔烃与脂肪酸的串联环化反应建立多环四氢呋喃

据报道，银催化的苯胺连接的1，7-烯炔与脂肪酸的串联环化反应。这种协同串联的环状结构可以直接有效地构建各种高度非对映选择性的多环四氢呋喃。伯酸和仲酸经历脱羧/级联自由基加成/α-C（sp ³）–H裂解/环烷基化/ O捕集以产生含氧[6.6.6.5]稠合产物。叔酸经过脱羧/级联自由基加成/β-C（sp ³）–H裂解/ O捕集得到含氧[6.6.6.6]熔融产物。

更新日期：2017-10-25

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