手性联萘基盒状铜催化的对映选择性串联迈克尔-酮醇缩合环加成反应，用于合成光学活性芳基和杂芳基稠合双环[2.2.2]辛烷。
Chiral Binaphthyl Box-Copper-Catalyzed Enantioselective Tandem Michael-Ketalization Annulations for Optically Active Aryl and Heteroaryl Fused Bicyclicnonanes.
机构信息
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou 215123, the People's Republic of China.
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, the People's Republic of China.
出版信息
Org Lett. 2020 May 15;22(10):3936-3941. doi: 10.1021/acs.orglett.0c01221. Epub 2020 May 1.
The combination of chiral binaphthyl box-copper(II) with triflimide (TfNH) was identified as an efficient catalytic system for the asymmetric Michael/ketalization of ()-2-hydroxyaryl-2-oxobut-3-enoates or ()-ethyl 4-(2-aminoaryl)-2-oxobut-3-enoates with pyrazolone derivatives. The corresponding asymmetric tandem reactions provided a series of enantioenriched aryl and heteroaryl fused 2,8-,- or ,-bicyclo[3.3.1]nonanes in high yields with excellent enantio- and diastereoselectivities.
手性联萘基 BOX-铜（II）与三氟甲磺酸根（TfNH）的组合被确定为高效的催化体系，可用于（）-2-羟基芳基-2-氧代丁-3-烯酸酯或（）-乙基 4-（2-芳基氨基）-2-氧代丁-3-烯酸酯与吡唑啉酮衍生物的不对称迈克尔/缩酮化反应。相应的不对称串联反应以高产率和优异的对映选择性和非对映选择性提供了一系列具有高对映体富集的芳基和杂芳基稠合的 2,8-，-或 ，-双环[3.3.1]壬烷。
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