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Copper(I)-Catalyzed Highly Enantioselective [3+3]-Cycloaddition of β-Aryl/Alkyl Vinyl Diazoacetates with Nitrones
Helvetica Chimica Acta ( IF 1.8 ) Pub Date : 2021-06-25 , DOI: 10.1002/hlca.202100081
Haifeng Zheng 1 , Isa Faghihi 1 , Michael P. Doyle 1
Affiliation  

β-Aryl/alkyl vinyl diazoacetates were investigated in metallo-vinylcarbene reactions with nitrones, revealing a Rh2(OAc)4-catalyzed cyclopropene dimerization reaction and a copper(I) catalyzed [3+3]-cycloaddition of nitrones. The chiral cyclopropyl-In-SaBox ligand with copper(I) catalysis could realize the asymmetric version of the cycloaddition reaction, delivering various 3,6-dihydro-1,2-oxazine derivatives in good yield and with excellent enantioselectivity under mild conditions.

中文翻译:

铜(I)-催化的β-芳基/烷基重氮乙酸乙烯酯与硝酮的高对映选择性[3+3]-环加成反应

在金属-乙烯基卡宾与硝酮的反应中研究了 β-芳基/烷基重氮乙酸酯,揭示了 Rh 2 (OAc) 4催化的环丙烯二聚反应和铜 (I) 催化的硝酮的 [3+3]-环加成反应。具有铜(I)催化的手性环丙基-In-SaBox配体可以实现环加成反应的不对称形式,在温和条件下以良好的收率和优异的对映选择性提供各种3,6-二氢-1,2-恶嗪衍生物。
更新日期:2021-07-16
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