Pd-catalyzed enantioselective cyclopropanation of nitriles with mono substituted allyl carbonates enabled by the bulky N-heterocyclic carbene ligand

Gao-Peng Zhang; Shuai Huang; Yang-Jie Jiang; Xiu-Yan Liu; Chang-Hua Ding; Yin Wei; Xue-Long Hou

doi:10.1039/C9CC01960J

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Pd-catalyzed enantioselective cyclopropanation of nitriles with mono substituted allyl carbonates enabled by the bulky N-heterocyclic carbene ligand†

Gao-Peng Zhang,^ab Shuai Huang,^ab Yang-Jie Jiang,^ab Xiu-Yan Liu,^a Chang-Hua Ding,^ac Yin Wei

*^a and Xue-Long Hou

*^ad

Author affiliations

* Corresponding authors

^a State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (SIOC), China
E-mail: weiyin@sioc.ac.cn, xlhou@sioc.ac.cn

^b University of Chinese Academy of Sciences, Beijing 100049, China

^c Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China

^d Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, SIOC, China

Abstract

A highly efficient catalyst for Pd-catalyzed cyclopropanation was developed using a bulkier N-heterocyclic carbene ligand, with which the nitriles reacted with mono substituted allyl reagents to afford cyclopropanes in high yields with high cyclopropanation/allylation and enantioselectivities. The reasons for cyclopropanation were investigated and the usefulness of the products was demonstrated.

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DOI: https://doi.org/10.1039/C9CC01960J
Article type: Communication
Submitted: 11 Mar 2019
Accepted: 09 May 2019
First published: 17 May 2019

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Chem. Commun., 2019,55, 6449-6452

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Pd-catalyzed enantioselective cyclopropanation of nitriles with mono substituted allyl carbonates enabled by the bulky N-heterocyclic carbene ligand

G. Zhang, S. Huang, Y. Jiang, X. Liu, C. Ding, Y. Wei and X. Hou, Chem. Commun., 2019, 55, 6449 DOI: 10.1039/C9CC01960J

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Chemical Communications

Pd-catalyzed enantioselective cyclopropanation of nitriles with mono substituted allyl carbonates enabled by the bulky N-heterocyclic carbene ligand†

Abstract

Supplementary files

Article information

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Pd-catalyzed enantioselective cyclopropanation of nitriles with mono substituted allyl carbonates enabled by the bulky N-heterocyclic carbene ligand

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