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由金属手性铑(III)配合物催化的乙烯基亚砜叶立德不对称合成手性环丙烷。

Asymmetric Synthesis of Chiral Cyclopropanes from Vinyl Sulfoxonium Ylides Catalyzed by a Chiral-at-Metal Rh(III) Complex.

作者信息

Xie Xiaoting, Zhao Zhifei, Wang Jun, Li Shi-Wu

机构信息

School of Chemistry and Chemical Engineering/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003, China.

Zhang Zhongjing School of Chinese Medicine, Nanyang Institute of Technology, Nanyang 473004, China.

出版信息

Org Lett. 2024 Sep 27;26(38):8144-8148. doi: 10.1021/acs.orglett.4c03051. Epub 2024 Sep 17.

Abstract

A chiral-at-metal Rh(III) complex-mediated [2+1] cyclization of vinyl sulfoxonium ylides with α,β-unsaturated 2,2-acylimidazoles has been demonstrated for the first time. This work provides a practical approach for assembling 1,2,3-trisubstituted chiral cyclopropane with alkyl structural units, which had advantages such as a wide range of substrates, good functional group tolerance, and mild reaction conditions. In addition, further amplification experiments and transformation of cycloaddition products were carried out to highlight the practicality of the method.

摘要

首次证明了一种手性金属铑(III)配合物介导的乙烯基亚砜叶立德与α,β-不饱和2,2-酰基咪唑的[2 + 1]环化反应。这项工作为组装具有烷基结构单元的1,2,3-三取代手性环丙烷提供了一种实用方法,该方法具有底物范围广、官能团耐受性好、反应条件温和等优点。此外,还进行了进一步的放大实验和环加成产物的转化,以突出该方法的实用性。

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