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

Journal of the American Chemical Society
Amberly B SanfordElizabeth R Jarvo

Abstract

Cross-electrophile coupling reactions of two Csp3-X bonds remain challenging. Herein we report an intramolecular nickel-catalyzed cross-electrophile coupling reaction of 1,3-diol derivatives. Notably, this transformation is utilized to synthesize 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. A procedure for direct transformation of 1,3-diols to cyclopropanes is also described. Calculations and experimental data are consistent with a nickel-catalyzed mechanism that begins with stereoablative oxidative addition at the secondary center.

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Citations

Jun 25, 2021·Journal of the American Chemical Society·Qi PanWangqing Kong
Aug 7, 2021·Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry·Amberly B Sanford, Elizabeth R Jarvo
Aug 26, 2020·Accounts of Chemical Research·Jiandong LiuHegui Gong
Sep 10, 2020·ACS Catalysis·Kelsey E PorembaSarah E Reisman
Oct 3, 2020·Organic Letters·Aiyou XiaYuanhong Liu
Apr 20, 2021·ACS Catalysis·Timothy B BoitNeil K Garg
Sep 28, 2021·Journal of the American Chemical Society·Wei-Yuan MaXing-Zhong Shu

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