Rh(I)-catalyzed Intramolecular [3+2] cycloaddition of trans-vinylcycloproplane-enes
Rh(I)-catalyzed Intramolecular [3+2] cycloaddition of trans-vinylcycloproplane-enes
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Rh(I) 催化的反式乙烯基环丙烯的分子内[3 2]环加成反应
DOI：
10.1021/ja8008715
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发表时间：
2008-06-11
影响因子：
15
通讯作者：
Yu, Zhi-Xiang
中科院分区：
文献类型：
--
作者：
Jiao, Lei;Ye, Siyu;Yu, Zhi-Xiang
乙烯基环丙烷（VCP）作为五碳组分而不是三碳组分，在过渡金属催化的环加成反应中得到了很好的应用。在这里，我们展示了Rh（I）催化的反式-VCP-烯的[3 + 2]反应，其中VCP充当三碳合成子以提供五元碳环。这种新的环加成反应能有效地从简单和容易制备的底物以良好的产率生成双环环戊烷。当使用顺式-VCP-烯作为底物时，VCP充当五碳单元以得到[5 + 2]环加合物。提出了VCP-烯的[3 + 2]和[5 + 2]环加成反应的简化方法。
Vinylcyclopropane (VCP) has been well applied as a five-carbon component, rather than a three-carbon component, in transition-metal catalyzed cycloadditions. Here we demonstrate a Rh(l)-catalyzed [3 + 2] reaction of trans-VCP-enes, where VCP acts as a three-carbon synthon to furnish five-membered carbocycles. This novel cycloaddition is efficient in generating bicyclic cyclopentanes in good yields from simple and easily prepared substrates. When cis-VCP-ene is used as the substrate, VCP acts as a five-carbon unit to give a [5 + 2] cycloadduct. Rationalization of the [3 + 2] and [5 + 2] cycloadditions of VCP-enes has been proposed.