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Enantioselective Multi-Component Cyclopropane Synthesis Enabled by Cu-Catalyzed Cyclopropene Carbometallation with Organoboron Reagent

preprint
submitted on 26.08.2018 and posted on 28.08.2018 by Zhanyu Li, Mengru Zhang, Yu Zhang, Shuang Liu, Jinbo Zhao, Qian Zhang
Deployment of organoboron in lieu of the strongly basic
organometallic reagents as carbon source in Cu-catalyzed
cyclopropene carbometallation opens unprecedented three-
component reactivity for stereoselective synthesis of poly-substituted cyclopropanes. A proof-of-principle demonstration of this novel carbometallation strategy is presented herein for a highly convergent access to poly-substituted aminocyclopropane framework via
carboamination. Preliminary results on asymmetric desymmetrization with commercial bisphosphine ligands attained high levels of enantioselection, offering a straightforward access to enantioenriched aminocyclopropanes bearing all-three chiral centers, including an all-carbon quaternary center. This strategy may underpin a host of novel synthetic protocols for poly-substituted cyclopropanes.

Funding

National Natural Science Foundation of China (21871045, 21831002), Natural Science Foundation of the Jilin Province (20160519003JH), Changbai Mountain Scholarship Program, and the Fundamental Research Funds for the Central Universities (2412017FZ014)

History

Email Address of Submitting Author

zhaojb100@mail.nenu.edu.cn

Institution

Northeast Normal University

Country

China

ORCID For Submitting Author

0000-0002-5261-7366

Declaration of Conflict of Interest

The authors declare no competing financial interest. A patent has been submitted based on this chemistry.

Version Notes

The orginial cif file was replaced with a revised one.

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