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Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes

Amberly B. Sanford, Taylor A. Thane, Tristan M. McGinnis, Pan-Pan Chen, Xin Hong* and Elizabeth R. Jarvo*

*Zhejiang University, Hangzhou, 310027, China; University of California, Irvine, California 92697-2025, United States, Email: hxchemzju.edu.cn, erjarvouci.edu

A. B. Sanford, T. A. Thane, T. M. MgGinnis, P.-P. Chen, X. Hong, E. R. Jarvo, J. Am. Chem. Soc., 2020, 142, 5017-5023.

DOI: 10.1021/jacs.0c01330 (free Supporting Information)



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Abstract

An intramolecular nickel-catalyzed cross-electrophile coupling reaction of 1,3-diol derivatives provides a range of mono- and 1,2-disubstituted alkylcyclopropanes, including those derived from terpenes, steroids, and aldol products. Additionally, enantioenriched cyclopropanes are synthesized from the products of proline-catalyzed and Evans aldol reactions.

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Key Words

cyclopropanes


ID: J48-Y2020