N-杂环卡宾催化的α,β-环状甲亚胺亚胺与芳基乙醛的立体选择性[3+2]环加成反应
N-Heterocyclic Carbene-Catalyzed Stereoselective [3 + 2] Cycloaddition of ,'-Cyclic Azomethine Imines with Aryl Acetaldehydes.
作者信息
Zhou Yipeng, Zhou Hongwei, Xu Jianfeng
机构信息
Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P.R. China.
College of Biological, Chemical Science and Engineering, Jiaxing University, 118 Jiahang Road, Jiaxing 314001, P.R. China.
出版信息
J Org Chem. 2022 Aug 5;87(15):10476-10484. doi: 10.1021/acs.joc.2c01064. Epub 2022 Jul 21.
A highly stereoselective [3 + 2] cycloaddition reaction of ,'-cyclic azomethine imines with aryl acetaldehydes enabled by a chiral N-heterocyclic carbene catalyst is accomplished, giving efficient access to a plethora of enantioenriched ,'-bicyclic pyrazolidinones featuring aromatic substituents at the C2 position. The current strategy can be directly conducted on a gram scale, and the product could be further reduced to bicyclic pyrazolidine without loss of enantiopurity.
在手性N-杂环卡宾催化剂的作用下，实现了α,β-环状偶氮甲碱亚胺与芳基乙醛的高立体选择性[3+2]环加成反应，从而能够高效地获得大量在C2位带有芳族取代基的对映体富集的α,β-双环吡唑烷酮。目前的策略可以直接在克级规模上进行，并且产物可以进一步还原为双环吡唑烷而不会损失对映体纯度。
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