Enantioselective Construction of Cyclobutanes: A New and Concise Approach to the Total Synthesis of (+)-Piperarborenine B
Enantioselective Construction of Cyclobutanes: A New and Concise Approach to the Total Synthesis of (+)-Piperarborenine B
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环丁烷的对映选择性构建：( )-Piperarborenine B 全合成的新且简洁的方法
DOI：
10.1021/jacs.6b08279
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发表时间：
2016-10-12
影响因子：
15
通讯作者：
Li, Xiaoge
中科院分区：
文献类型：
--
作者：
Hu, Jiang-Lin;Feng, Liang-Wen;Li, Xiaoge
发展了一种高非对映选择性和对映选择性的Cu（II）/SaBOX催化的亚甲基丙二酸酯与多取代烯烃的[2 + 2]环加成反应，以高产率得到光学活性的环丁烷，其dr>99/1，ee>99%。从亚甲基丙二酸酯和烯烃经八步完成（+）-胡椒冰片烯B的全合成，总收率为17%，DR>99/1，ee> 99%。
A highly diastereoselective and enantioselective Cu(II)/SaBOX-catalyzed [2 + 2] cycloaddition of methylidenemalonate and multisubstituted alkenes was developed to furnish optically active cyclobutanes in high yields with >99/1 dr and up to >99% ee. By application of the newly developed method, the total synthesis of (+)-piperarborenine B was completed in eight steps from methylidenemalonate and olefin in 17% overall yield with >99/1 dr and 99% ee.