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Their synthesis commonly relies on asymmetric cyclopropanation of diazo compounds, potentially explosive and needing stabilizing substituents. Thus, asymmetric catalytic transformations of non\u2010stabilized carbenes or carbenoids remain a formidable challenge. Herein, we report the unprecedented chromium\u2010catalyzed asymmetric cyclopropanation of readily available\n                    <jats:italic>gem<\/jats:italic>\n                    \u2010dihaloalkanes and terminal olefins. Distinct from previous approaches,\n                    <jats:italic>gem<\/jats:italic>\n                    \u2010dihaloalkanes serve as suitable precursors for non\u2010stabilized carbenes or carbenoids, furnishing various functionalized chiral cyclopropanes. Mechanistic studies, including radical trapping, non\u2010linear effect, and UV\/Vis spectroscopy, provide insights into the catalytic process, featuring radical\u2010polar crossover.\n                  <\/jats:p>","DOI":"10.1002\/anie.202305987","type":"journal-article","created":{"date-parts":[[2023,5,10]],"date-time":"2023-05-10T23:49:44Z","timestamp":1683762584000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":42,"title":["Catalytic Diastereo\u2010 and Enantioselective Cyclopropanation of\n                    <i>gem<\/i>\n                    \u2010Dihaloalkanes and Terminal Olefins"],"prefix":"10.1002","volume":"62","author":[{"given":"Hou\u2010Lu","family":"Liu","sequence":"first","affiliation":[{"name":"Department of Chemistry Zhejiang University  Hangzhou 310058 China"},{"name":"Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province Department of Chemistry School of Science Westlake 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