cis-2,3-Disubstituted cyclopropane 1,1-diesters in [3 + 2] annulations with aldehydes: highly diastereoselective construction of densely substituted tetrahydrofurans.
cis-2,3-Disubstituted cyclopropane 1,1-diesters in [3 + 2] annulations with aldehydes: highly diastereoselective construction of densely substituted tetrahydrofurans.
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DOI：
10.1021/jo400554a
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发表时间：
2013-05
期刊：
影响因子：
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通讯作者：
Gaosheng Yang;Yongxian Sun;Yue-Ling Shen;Zhuo Chai;Shuangliu Zhou;Jiang Chu;Jung-Hyeon Chai
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文献类型：
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作者：
Gaosheng Yang;Yongxian Sun;Yue-Ling Shen;Zhuo Chai;Shuangliu Zhou;Jiang Chu;Jung-Hyeon Chai
在AlCl3促进的[3+2]-与醛的环化反应中，考察了一系列顺-2，3-二取代环丙烷1，1-二酯。在该反应中，这些顺式环丙烷表现出与反式环丙烷截然不同的反应活性，化学产率高(高达98%)，并提供了理想的环状产物，具有良好的非对映异构体纯度。这一方案提供了一种简便和高度立体选择性的方法来构建合成有用的五取代四氢呋喃，而用其他方法不易获得。
A series of cis-2,3-disubstituted cyclopropane 1,1-diesters were examined in the AlCl3-promoted [3 + 2]-annulations with aldehydes. In this reaction, these cis-cyclopropanes displayed reactivities starkly different from their trans counterparts in terms of the high chemical yields (up to 98%) and provided the desired annulation products with excellent diastereomeric purity. This protocol provides a facile and highly stereoselective way to construct synthetically useful pentasubstituted tetrahydrofurans not easily accessible using other methods.