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手性转移在铑(I)催化的乙烯基氮丙啶和肟醚的[3 + 2]-环加成反应中的应用:手性咪唑烷的原子经济性合成。

Chirality Transfer in Rhodium(I)-Catalyzed [3 + 2]-Cycloaddition of Vinyl Aziridines and Oxime Ethers: Atom-Economical Synthesis of Chiral Imidazolidines.

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering , East China Normal University , 3663 N. Zhongshan Road , Shanghai 200062 , P. R. China.

出版信息

Org Lett. 2018 Jun 15;20(12):3587-3590. doi: 10.1021/acs.orglett.8b01378. Epub 2018 Jun 4.

DOI:10.1021/acs.orglett.8b01378
PMID:29863882
Abstract

A highly efficient and stereoselective synthesis of enantioenriched imidazolidines by rhodium-catalyzed intermolecular [3 + 2] cycloaddition reaction of chiral vinyl aziridines and oxime ethers has been successfully developed. Notably, both aldoximes and ketoximes are suitable substrates to afford the corresponding chiral imidazolidines in high yields with good stereoselectivity. This transformation represents an unprecedented example that utilizes ketimine derivatives as an aza-[2C]-component in cycloadditions of vinyl aziridines.

摘要

通过手性乙烯基氮丙啶与肟醚的铑催化的分子间[3+2]环加成反应,成功地开发了一种高效和立体选择性的手性咪唑烷的合成方法。值得注意的是,醛肟和酮肟都是合适的底物,以高产率和良好的立体选择性得到相应的手性咪唑烷。这种转化代表了利用亚胺衍生物作为乙烯基氮丙啶环加成的aza-[2C]-组分的空前实例。

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Chirality Transfer in Rhodium(I)-Catalyzed [3 + 2]-Cycloaddition of Vinyl Aziridines and Oxime Ethers: Atom-Economical Synthesis of Chiral Imidazolidines.手性转移在铑(I)催化的乙烯基氮丙啶和肟醚的[3 + 2]-环加成反应中的应用:手性咪唑烷的原子经济性合成。
Org Lett. 2018 Jun 15;20(12):3587-3590. doi: 10.1021/acs.orglett.8b01378. Epub 2018 Jun 4.
2
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