Enantioselective Formal [4+1] Cycloaddition of Diazoarylacetates and the Danishefsky's Diene: Stereoselective Synthesis of (-)-1,13-Herbertenediol
Enantioselective Formal [4+1] Cycloaddition of Diazoarylacetates and the Danishefsky's Diene: Stereoselective Synthesis of (-)-1,13-Herbertenediol
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对映选择性缩甲醛 [4 1] 重氮芳基乙酸酯和达尼塞夫斯基二烯的环加成：(-)-1,13-Herbertenediol 的立体选择性合成
DOI：
10.1021/acs.joc.8b01546
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发表时间：
2018
影响因子：
3.6
通讯作者：
Liu Quan-Zhong
中科院分区：
文献类型：
--
作者：
Hu Fang;Zhou Qing;Cao Fei;Chu Wen-Dao;He Long;Liu Quan-Zhong
在铑手性二烯络合物催化下，α-重氮芳基乙酸芳基酯与富电子Danishefsky型二烯的对映选择性环加成反应得到了高官能化、光学富集的环戊烯酮，产率高达97%，对映选择性为60- 92%ee.采用光学富集的具有全碳季中心的环戊烯酮作为关键中间体，成功地合成了（−）-1，13-Herbertenediol，总收率为25%。
Rodium chiral diene complex-catalyzed enantioselective cycloaddition of aryl α-diazoarylacetates and electron-enriched Danishefsky-type dienes afforded highly functionalized and optically enriched cyclopentenones in excellent yields (up to 97% yield) and with good to excellent enantioselectivities (60–92% ee). (−)-1,13-Herbertenediol was successfully synthesized in an overall 25% yield employing the optically enriched cyclopentenone with an all-carbon quaternary center as the key intermediate.