Stereocontrolled Synthesis of trans/cis-2,3-Disubstituted Cyclopropane-1,1-diesters and Applications in the Syntheses of Furanolignans
Stereocontrolled Synthesis of trans/cis-2,3-Disubstituted Cyclopropane-1,1-diesters and Applications in the Syntheses of Furanolignans
复制标题
反式/顺式-2,3-二取代环丙烷-1,1-二酯的立体控制合成及其在呋喃木脂素合成中的应用
DOI：
10.1021/acs.joc.8b01798
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发表时间：
2018
影响因子：
3.6
通讯作者：
Chai Zhuo
中科院分区：
文献类型：
--
作者：
Shen Yue;Chai Jun;Yang Gaosheng;Chen Wenlong;Chai Zhuo
A new Michael addition/intramolecular alkylation sequence of (Z)-3-(2-bromo-3-arylacryloyl)oxazolidin-2-ones and malonates was developed. By a simple switch of the reaction conditions including the base promoter, solvent, and reaction temperature, both of thecis- andtrans-isomers of a series of oxazolidinone-containing 2,3-disubstituted cyclopropane-1,1-diesters could be obtained in good-to-excellent yields and with an excellent diastereoselectivity. The utility of the cyclopropane products was demonstrated in the diastereoselective syntheses of (±)-urinaligran and a stereoisomer of (±)-virgatusin involving the AlCl3-promoted [3+2] annulation with veraldehyde or piperonal as the key step.
