铜催化的达尼谢夫斯基双烯与β,γ-不饱和α-酮酯的对映选择性杂-狄尔斯-阿尔德反应。
Copper-catalyzed enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with β,γ-unsaturated α-ketoesters.
作者信息
Hu Yanbin, Xu Kun, Zhang Sheng, Guo Fengfeng, Zha Zhenggen, Wang Zhiyong
机构信息
Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry & Collaborative Innovation Center of Suzhou Nano Science and Technology, University of Science and Technology of China , Hefei, Anhui 230026, P. R. China.
出版信息
Org Lett. 2014 Jul 3;16(13):3564-7. doi: 10.1021/ol5015009. Epub 2014 Jun 23.
A highly enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with β,γ-unsaturated α-ketoesters was developed for the first time by virtue of chiral copper complexes. This protocol provided a facile access to optically active dihydropyranones bearing a quaternary center with high enantioselectivities and good yields. Furthermore, on the basis of the isolated intermediate analysis, the reaction pathway was substrate-dependent.
首次利用手性铜配合物实现了达尼谢夫斯基双烯与β,γ-不饱和α-酮酯的高度对映选择性杂环狄尔斯-阿尔德反应。该方法提供了一种简便的途径，可高对映选择性和高收率地获得带有季碳中心的光学活性二氢吡喃酮。此外，基于对分离出的中间体的分析，反应途径取决于底物。
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