(4+3) cycloadditions of allenyl ether-derived oxygen-stabilized oxyallyls with furans
(4+3) cycloadditions of allenyl ether-derived oxygen-stabilized oxyallyls with furans
复制标题
(4 3) 烯基醚衍生的氧稳定的草烯丙基与呋喃的环加成
DOI：
10.1039/c9qo01349k
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发表时间：
2020-01-21
影响因子：
5.4
通讯作者：
He, Shuzhong
中科院分区：
文献类型：
--
作者：
Huang, Xian;Thor, Waygen;He, Shuzhong
研究了联烯醚与呋喃的（4 + 3）环加成反应。该反应的特点是在H2 PO 4-存在下，通过丙二烯基醚的环氧化原位形成氧稳定的氧化烯丙基。利用DFT计算研究了氧稳定的氧烯丙基物种和H2 PO 4-之间的多重相互作用，以合理化该环加成反应的区域和非对映选择性。通过将（4 + 3）环加合物分两步转化为弗罗多辛B的环庚[B]苯并呋喃骨架，证明了这种环加成的效用。
(4 + 3) cycloadditions between allenyl ethers and furans are described. The reaction features an in situ formation of oxygen-stabilized oxyallyls via epoxidations of allenyl ethers in the presence of H2PO4-. The multiple interactions between the oxygen-stabilized oxyallyl species and H2PO4- were studied using DFT calculations for rationalization of the regio- and diastereoselectivity of this cycloaddition. The utilities of this cycloaddition have been demonstrated by converting the (4 + 3) cycloadduct into the cyclohepta[b]benzofuran skeleton of frondosin B in two steps.