Affiliation:
1. Department of Chemistry Zhejiang University Hangzhou 310058 China
2. Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province Department of Chemistry School of Science Westlake University Hangzhou 310024 China
3. Institute of Natural Sciences Westlake Institute for Advanced Study Hangzhou 310024 Zhejiang Province China
Abstract
AbstractChiral cyclopropane derivatives are essential in synthetic chemistry and drug discovery. Their synthesis commonly relies on asymmetric cyclopropanation of diazo compounds, potentially explosive and needing stabilizing substituents. Thus, asymmetric catalytic transformations of non‐stabilized carbenes or carbenoids remain a formidable challenge. Herein, we report the unprecedented chromium‐catalyzed asymmetric cyclopropanation of readily available gem‐dihaloalkanes and terminal olefins. Distinct from previous approaches, gem‐dihaloalkanes serve as suitable precursors for non‐stabilized carbenes or carbenoids, furnishing various functionalized chiral cyclopropanes. Mechanistic studies, including radical trapping, non‐linear effect, and UV/Vis spectroscopy, provide insights into the catalytic process, featuring radical‐polar crossover.
Funder
National Natural Science Foundation of China
Subject
General Chemistry,Catalysis
Cited by
2 articles.
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