An Atom-Economic Synthesis of Bicyclo[3.1.0]hexanes by Rhodium N-Heterocyclic Carbene-Catalyzed Diastereoselective Tandem Hetero-[5+2] Cycloaddition/Claisen Rearrangement Reaction of Vinylic Oxiranes with Alkynes
An Atom-Economic Synthesis of Bicyclo[3.1.0]hexanes by Rhodium N-Heterocyclic Carbene-Catalyzed Diastereoselective Tandem Hetero-[5+2] Cycloaddition/Claisen Rearrangement Reaction of Vinylic Oxiranes with Alkynes
复制标题
N-杂环卡宾铑催化乙烯基环氧乙烷与炔烃的非对映选择性串联杂-[5 2]环加成/克莱森重排反应原子经济合成双环[3.1.0]己烷
DOI：
10.1021/ja2014604
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发表时间：
2011-05-18
影响因子：
15
通讯作者：
Zhang, Junliang
中科院分区：
文献类型：
--
作者：
Feng, Jian-Jun;Zhang, Junliang
报道了乙烯基环氧乙烷作为含杂原子的五原子组分在过渡金属催化的环加成反应中的首次合成应用。一种新的，有效的，非对映选择性串联分子内杂-[5 + 2]环加成/Claisen重排的乙烯基环氧乙烷-炔底物，使用铑NHC络合物，并提供战略新颖的，原子经济的，区域特异性，和非对映选择性的访问[3.1.0]双环产品已被开发。
The first synthetic application of a vinylic oxirane as a heteroatom-containing five-atom component in transition-metal-catalyzed cycloaddition reactions is reported. A new, efficient, diastereoselective tandem intramolecular hetero-[5 + 2] cycloaddition/Claisen rearrangement of vinylic oxirane-alkyne substrates that uses a rhodium NHC complex and provides strategically novel, atom-economic, regiospecific, and diastereoselective access to [3.1.0] bicyclic products has been developed.