Integration of electrooxidative cyclization and chemical oxidation via alkoxysulfonium ions. Synthesis of exocyclic ketones from alkenes with cyclization
Integration of electrooxidative cyclization and chemical oxidation via alkoxysulfonium ions. Synthesis of exocyclic ketones from alkenes with cyclization
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DOI：
10.1039/c3ob40315g
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发表时间：
2013-01-01
影响因子：
3.2
通讯作者：
Yoshida, Jun-ichi
中科院分区：
文献类型：
--
作者：
Ashikari, Yosuke;Nokami, Toshiki;Yoshida, Jun-ichi
实现了电氧化环化和化学氧化的集成。在DMSO存在下，具有亲核部分的烯烃的电化学氧化得到环化的烷氧基锍离子，其通过用三乙胺以一锅顺序方式处理而转化为相应的酮。该方法也是一种有效的工具，环化的1，6-二烯提供五元环二酮在高立体选择性。
An integration of electrooxidative cyclization and chemical oxidation was achieved. Electrochemical oxidation of alkenes having a nucleophilic moiety in the presence of DMSO gave cyclized alkoxysulfonium ions, which were converted to the corresponding ketones by treatment with triethylamine in a one-pot sequential manner. The method is also an effective tool for cyclization of 1,6-dienes affording five-membered ring diketones in high stereoselectivity.