Highly enantioselective [2+2]-cycloaddition reactions catalyzed by a chiral aluminum bromide complex
Highly enantioselective [2+2]-cycloaddition reactions catalyzed by a chiral aluminum bromide complex
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DOI：
10.1021/ja0765262
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发表时间：
2007-10-24
影响因子：
15
通讯作者：
Corey, E. J.
中科院分区：
文献类型：
--
作者：
Canales, Eda;Corey, E. J.
手性环丁烷的对映选择性[2+2]-环加成途径是罕见的，通常不用于合成。本文报道了在手性恶唑硼烷-AlBr_3络合物催化下，乙烯基醚与丙烯酸三氟乙酯的环加成反应，得到了[2+2]-加成物，产率高，对映选择性好。这些加合物的合成有价值的中间体的应用也被提出。
Enantioselective [2+2]-cycloaddition pathways to chiral cyclobutanes are rare and not generally utilized for synthesis. A new cycloaddition reaction of vinyl ethers with trifluoroethyl acrylate in the presence of a catalytic amount of chiral oxazaborolidine-AlBr3 complex is described which affords [2+2]-adducts with excellent yields and enantioselectivities. Applications of these adducts to the synthesis of synthetically valuable intermediates are also presented.