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Evaluation of the transition states for insertion and for hydrolysis of intermediate complexes (which were emphasized in response to the experimental results) using DFT calculations at the B97D/6‐31G(d) level with the LANL2DZ basis set for rhodium revealed that: (i) the electron‐poor nature of the ligands and (ii) CH–π interactions between the ligand and coumarin substrates played significant roles in both acceleration of insertion and inhibition of ArB(OH)<jats:sub>2</jats:sub> decomposition (protodeboronation). The computationally‐designed ligand, incorporating the above information, enabled a decrease in the catalyst loading to 0.025 mol% (S/C=4,000), which is less than one one‐hundredth relative to past catalyst loadings of typically 3 mol%, with almost complete enantioselectivity. Furthermore, the gram‐scale synthesis of the urological drug, (<jats:italic>R</jats:italic>)‐tolterodine (<jats:sc>l</jats:sc>)‐tartrate, was demonstrated without the need of intermediate purification.</jats:p><jats:p><jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:graphic xmlns:xlink=\"http://www.w3.org/1999/xlink\" mimetype=\"image/png\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic/adsc201701191-toc-0001-m.png\"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:boxed-text>\n</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1420845751153889920","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"70335579"},{"@type":"NRID","@value":"1000070335579"},{"@type":"NRID","@value":"9000005195150"},{"@type":"NRID","@value":"9000258420829"},{"@type":"NRID","@value":"9000258420374"},{"@type":"NRID","@value":"9000409486161"},{"@type":"NRID","@value":"9000369734663"},{"@type":"NRID","@value":"9000248213388"},{"@type":"NRID","@value":"9000258419368"},{"@type":"NRID","@value":"9000000037205"},{"@type":"NRID","@value":"9000000842232"},{"@type":"NRID","@value":"9000408668737"},{"@type":"NRID","@value":"9000258420536"},{"@type":"NRID","@value":"9000256024238"},{"@type":"NRID","@value":"9000254710955"},{"@type":"NRID","@value":"9000258419375"},{"@type":"NRID","@value":"9000387917072"},{"@type":"NRID","@value":"9000240082920"},{"@type":"NRID","@value":"9000256022795"},{"@type":"NRID","@value":"9000388500180"},{"@type":"NRID","@value":"9000258420694"},{"@type":"NRID","@value":"9000024954419"},{"@type":"NRID","@value":"9000404149182"},{"@type":"NRID","@value":"9000258420932"},{"@type":"NRID","@value":"9000309169262"},{"@type":"NRID","@value":"9000010714494"},{"@type":"NRID","@value":"9000408668740"},{"@type":"NRID","@value":"9000256023003"},{"@type":"NRID","@value":"9000018970637"},{"@type":"RESEARCHMAP","@value":"https://researchmap.jp/read0074450"}],"foaf:name":[{"@value":"Toshinobu Korenaga"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry and Biological Sciences, Faculty of Science and Engineering Iwate University  4-3-5 Ueda Morioka, Iwate 020-8551 Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004229883144320","@type":"Researcher","foaf:name":[{"@value":"Ryo Sasaki"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry and Biological Sciences, Faculty of Science and Engineering Iwate University  4-3-5 Ueda Morioka, Iwate 020-8551 Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004229883144451","@type":"Researcher","foaf:name":[{"@value":"Toshihide Takemoto"}],"jpcoar:affiliationName":[{"@value":"Central Research Laboratory, Technology and Development Division Kanto Chemical Co., Inc., Soka  Saitama 340-0003 Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004229883144713","@type":"Researcher","foaf:name":[{"@value":"Toshihisa Yasuda"}],"jpcoar:affiliationName":[{"@value":"Central Research Laboratory, Technology and Development Division Kanto Chemical Co., Inc., Soka  Saitama 340-0003 Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004229883144712","@type":"Researcher","foaf:name":[{"@value":"Masahito Watanabe"}],"jpcoar:affiliationName":[{"@value":"Central Research Laboratory, Technology and Development Division Kanto Chemical Co., Inc., Soka  Saitama 340-0003 Japan"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"16154150"},{"@type":"EISSN","@value":"16154169"}],"prism:publicationName":[{"@value":"Advanced Synthesis & Catalysis"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"2018-01-11","prism:volume":"360","prism:number":"2","prism:startingPage":"322","prism:endingPage":"333"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fadsc.201701191"},{"@id":"https://advanced.onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.201701191"}],"createdAt":"2017-11-06","modifiedAt":"2025-10-06","project":[{"@id":"https://cir.nii.ac.jp/crid/1040000781911582336","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"16K05764"},{"@type":"JGN","@value":"JP16K05764"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-16K05764/"}],"notation":[{"@language":"ja","@value":"新型活性種を鍵とした有機分子触媒による触媒的空気酸化反応の開発"},{"@language":"en","@value":"Development of catalytic aerial oxidation using oranocatalyst"}]}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360002214465533312","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"The Origins of Enantioselectivity in Rh–Diene Complex Catalysed Arylation of Cyclohex‐2‐enones"}]},{"@id":"https://cir.nii.ac.jp/crid/1360002219099655296","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Polar Substituent Constants for Substituted Phenyl Groups. 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