Hydrazulene ring systems via heteroatom-assisted [1,2]-shift of oxonium and sulfonium ylides
Hydrazulene ring systems via heteroatom-assisted [1,2]-shift of oxonium and sulfonium ylides
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DOI：
10.1021/ol050396p
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发表时间：
2005-04-28
期刊：
影响因子：
5.2
通讯作者：
West, FG
中科院分区：
文献类型：
--
作者：
Murphy, GK;West, FG
具有侧链重氮酮的环状混合缩醛在用Cu（hfacac）（2）-氧鎓叶立德的Stevens [1，2]-位移处理时发生重排，形成醚桥环庚烷环体系，主要产物（7），在某些情况下伴随有少量由锍叶立德的（1，2]-位移产生的产物（8）。在随后的硫触发的桥连醚裂解中，得到所需的双环[5.3.0]庚烯，沿着新的S（N）2'攻击所得烯丙基缩酮的产物。
Cyclic mixed acetals with pendant diazoketone side chains undergo rearrangement to ether-bridged cycloheptane ring systems on treatment with Cu(hfacac)(2)- Stevens [1,2]-shift of an oxonium ylide furnishes the major product (7), in some cases accompanied by minor amounts of a product (8) resulting from (1,2]-shift of a sulfonium ylide. In the subsequent sulfur-triggered cleavage of the bridging ether, the desired bicyclo[5.3.0]heptene was obtained, along with the product of novel S(N)2' attack on the resulting allylic ketal.