Synthesis of planar chiral ferrocenes via a Pd(0)-catalyzed syn-carbopalladation/asymmetric C–H alkenylation process

Lixiang Jia; Xiaobing Liu; An-An Zhang; Tao Wang; Yuanzhao Hua; Heng Li; Lantao Liu

doi:10.1039/C9CC06529F

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Synthesis of planar chiral ferrocenes via a Pd(0)-catalyzed syn-carbopalladation/asymmetric C–H alkenylation process†

Lixiang Jia,^ab Xiaobing Liu,^a An-An Zhang,^a Tao Wang,

^a Yuanzhao Hua,^b Heng Li^b and Lantao Liu

*^abc

Author affiliations

* Corresponding authors

^a Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000, P. R. China
E-mail: liult05@iccas.ac.cn

^b College of Chemistry, Zhengzhou University, Zhengzhou 450001, P. R. China

^c Beijing National Laboratory for Molecular Sciences (BNLMS), College of Chemistry, Peking University, Beijing 100871, P. R. China

Abstract

The Pd(0)-catalyzed tandem intermolecular syn-carbopalladation/asymmetric C–H alkenylation reaction of N-ferrocenyl propiolamides with aryl iodides has been realized, generating planar chiral ferrocene[1,2-d] pyrrolinones in good yields. Through employing BINOL-derived phosphoramidite ligands, up to 95% ee is achieved.

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Article information

DOI: https://doi.org/10.1039/C9CC06529F
Article type: Communication
Submitted: 27 Aug 2019
Accepted: 02 Jan 2020
First published: 04 Jan 2020

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Chem. Commun., 2020,56, 1737-1740

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Synthesis of planar chiral ferrocenes via a Pd(0)-catalyzed syn-carbopalladation/asymmetric C–H alkenylation process

L. Jia, X. Liu, A. Zhang, T. Wang, Y. Hua, H. Li and L. Liu, Chem. Commun., 2020, 56, 1737 DOI: 10.1039/C9CC06529F

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Chemical Communications

Synthesis of planar chiral ferrocenes via a Pd(0)-catalyzed syn-carbopalladation/asymmetric C–H alkenylation process†

Abstract

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Synthesis of planar chiral ferrocenes via a Pd(0)-catalyzed syn-carbopalladation/asymmetric C–H alkenylation process

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