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Here, we report a formal cyclopropylation of imines with cyclopropanols, enabling the construction of previously inaccessible cyclopropane\u2010embedded \u03b3\u2010amino alcohols. This transformation leverages the unique reactivity of enolized zinc homoenolates, which effectively act as a \u03b2\u2010hydroxycyclopropyl anions and engage imines through a sequence of Mannich addition and ring closure. The key to this reactivity lies in the use of bulky\n                    <jats:italic>N<\/jats:italic>\n                    \u2010heterocyclic carbene (NHC) ligands, which promote efficient coupling with\n                    <jats:italic>N<\/jats:italic>\n                    \u2010sulfonyl aldimines as well as chiral\n                    <jats:italic>N<\/jats:italic>\n                    \u2010sulfinyl trifluoromethyl\u2010ketimines while ensuring excellent diastereocontrol over three contiguous stereocenters. Furthermore, the resulting \u03b3\u2010amino alcohols can be transformed into \u03b2\u2010 or \u03b3\u2010aminofunctionalized ketones via homoenolate or \u03b2\u2010keto radical intermediates, offering versatile platforms for downstream derivatization.\n                  <\/jats:p>","DOI":"10.1002\/anie.202511646","type":"journal-article","created":{"date-parts":[[2025,8,12]],"date-time":"2025-08-12T06:54:37Z","timestamp":1754981677000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Formal Cyclopropylation of Imines with Cyclopropanols: Stereocontrolled Access to Conformationally Constrained \u03b3\u2010Amino Alcohols"],"prefix":"10.1002","volume":"64","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3958-7369","authenticated-orcid":false,"given":"Kento","family":"Tsukiji","sequence":"first","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Tohoku University  6\u20103 Aoba, Aramaki Sendai 980\u20138578 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kazuya","family":"Kanemoto","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Tohoku University  6\u20103 Aoba, Aramaki Sendai 980\u20138578 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1987-3392","authenticated-orcid":false,"given":"Eunsang","family":"Kwon","sequence":"additional","affiliation":[{"name":"Research and Analytical Center for Giant Molecules Graduate School of Science Tohoku University  Sendai 980\u20138578 Japan"},{"name":"Endowed Research Laboratory of Dimensional Integrated Nanomaterials Graduate School of Science Tohoku University  Sendai 980\u20138578 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8997-3268","authenticated-orcid":false,"given":"Naohiko","family":"Yoshikai","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Tohoku University  6\u20103 Aoba, Aramaki Sendai 980\u20138578 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,8,11]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr050065q"},{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0MD00370K"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.6b00472"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2024.117980"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm3008739"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2018.10.041"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja107857v"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol050791f"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr068373r"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr0684016"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr980414z"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja026292g"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0363462"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b03356"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c07117"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200901054"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c10109"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c04331"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.202300114"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202412456"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/advs.202307633"},{"key":"e_1_2_6_22_1","first-page":"1","volume":"77","author":"Cha J. 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