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This study presents a method for regioselectivity switching in the aldol reactions of cyclic\n                    <jats:italic>Ge<\/jats:italic>\n                    \u2010dienolates, which are generated from the (4 + 1) cycloaddition of allenoates with Ge(II) salts. Through systematic tuning of the charge and orbital distributions of the\n                    <jats:italic>Ge<\/jats:italic>\n                    \u2010dienolates and their aldehyde reaction partners, regio\u2010 and stereoselective access to three distinct aldol adducts (\n                    <jats:italic>syn<\/jats:italic>\n                    \u2010\n                    <jats:italic>\u03b1<\/jats:italic>\n                    \u2010,\n                    <jats:italic>anti<\/jats:italic>\n                    \u2010\n                    <jats:italic>\u03b1<\/jats:italic>\n                    \u2010, and\n                    <jats:italic>anti<\/jats:italic>\n                    \u2010\n                    <jats:italic>\u03b3<\/jats:italic>\n                    \u2010adducts) is achieved. The aldol reaction of\n                    <jats:italic>Ge<\/jats:italic>\n                    \u2010dienolates generally proceeds via an orbital\u2010controlled pathway to afford the\n                    <jats:italic>anti<\/jats:italic>\n                    \u2010\n                    <jats:italic>\u03b3<\/jats:italic>\n                    \u2010adduct through a cyclic transition state. Activation of the aldehyde with a Lewis acid shifts the reaction to a charge\u2010controlled pathway, resulting in the\n                    <jats:italic>syn<\/jats:italic>\n                    \u2010\n                    <jats:italic>\u03b1<\/jats:italic>\n                    \u2010adduct via an acyclic transition state. Notably, coordination of a ligand or solvent to the Ge center of the cyclic\n                    <jats:italic>Ge<\/jats:italic>\n                    \u2010dienolates increases electron density, thereby favoring a charge\u2010controlled pathway, promoting selective\n                    <jats:italic>\u03b1<\/jats:italic>\n                    \u2010addition to yield the\n                    <jats:italic>anti<\/jats:italic>\n                    \u2010\n                    <jats:italic>\u03b1<\/jats:italic>\n                    \u2010adduct through a distinct cyclic transition state. The synthetic utility of these types of adducts is further demonstrated via gold\u2010catalyzed intramolecular C\u2500H\/C\u2013Ge cross\u2010coupling, which enables the efficient synthesis of various fused\u2010ring systems.\n                  <\/jats:p>","DOI":"10.1002\/chem.71422","type":"journal-article","created":{"date-parts":[[2026,7,17]],"date-time":"2026-07-17T13:57:29Z","timestamp":1784296649000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Regioselective Aldol Reactions Directed by Charge and Orbital Effects in Cyclic Germyl Dienolates: Synthesis of Three Distinct Regio\u2010 and Stereoisomers"],"prefix":"10.1002","volume":"32","author":[{"ORCID":"https:\/\/orcid.org\/0009-0009-8362-9149","authenticated-orcid":false,"given":"Taishi","family":"Nojima","sequence":"first","affiliation":[{"name":"Department of Applied Chemistry Graduate School of Engineering The University of Osaka  Suita Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3438-786X","authenticated-orcid":false,"given":"Akihito","family":"Konishi","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Graduate School of Engineering The University of Osaka  Suita Osaka Japan"},{"name":"Innovative Catalysis Science Division Institute for Open and Transdisciplinary Research Initiatives (ICS\u2010OTRI) The University of Osaka  Suita Osaka Japan"},{"name":"Center for Future Innovation Graduate School of Engineering The University of Osaka  Suita Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6618-2893","authenticated-orcid":false,"given":"Makoto","family":"Yasuda","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Graduate School of Engineering The University of Osaka  Suita Osaka Japan"},{"name":"Innovative Catalysis Science Division Institute for Open and Transdisciplinary Research Initiatives (ICS\u2010OTRI) The University of Osaka  Suita Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,7,17]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/9780470689493"},{"key":"e_1_2_7_3_1","volume-title":"Physical Organic Chemistry","author":"Isaacs N. 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