{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,2]],"date-time":"2025-11-02T09:18:14Z","timestamp":1762075094710,"version":"build-2065373602"},"reference-count":43,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2022,11,13]],"date-time":"2022-11-13T00:00:00Z","timestamp":1668297600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001691","name":"JSPS KAKENHI","doi-asserted-by":"publisher","award":["C 20K06945"],"award-info":[{"award-number":["C 20K06945"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Recently, catalytic enantioselective syntheses of N-C axially chiral compounds have been reported by many groups. Most N-C axially chiral compounds prepared through a catalytic asymmetric reaction possess carboxamide or nitrogen-containing aromatic heterocycle skeletons. On the other hand, although N-C axially chiral sulfonamide derivatives are known, their catalytic enantioselective synthesis is relatively underexplored. We found that the reaction (Tsuji\u2013Trost allylation) of allyl acetate with secondary sulfonamides bearing a 2-arylethynyl-6-methylphenyl group on the nitrogen atom proceeds with good enantioselectivity (up to 92% ee) in the presence of (S,S)-Trost ligand-(allyl-PdCl)2 catalyst, affording rotationally stable N-C axially chiral N-allylated sulfonamides. Furthermore, the absolute stereochemistry of the major enantiomer was determined by X-ray single crystal structural analysis and the origin of the enantioselectivity was considered.<\/jats:p>","DOI":"10.3390\/molecules27227819","type":"journal-article","created":{"date-parts":[[2022,11,14]],"date-time":"2022-11-14T04:24:10Z","timestamp":1668399850000},"page":"7819","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Catalytic Enantioselective Synthesis of N-C Axially Chiral N-(2,6-Disubstituted-phenyl)sulfonamides through Chiral Pd-Catalyzed N-Allylation"],"prefix":"10.3390","volume":"27","author":[{"given":"Sota","family":"Fukasawa","sequence":"first","affiliation":[{"name":"Department of Applied Chemistry (Japanese Association of Bio-Intelligence for Well-Being), Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tatsuya","family":"Toyoda","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry (Japanese Association of Bio-Intelligence for Well-Being), Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ryohei","family":"Kasahara","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry (Japanese Association of Bio-Intelligence for Well-Being), Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chisato","family":"Nakamura","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry (Japanese Association of Bio-Intelligence for Well-Being), Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yuuki","family":"Kikuchi","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry (Japanese Association of Bio-Intelligence for Well-Being), Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0969-8500","authenticated-orcid":false,"given":"Akiko","family":"Hori","sequence":"additional","affiliation":[{"name":"Graduate School of Engineering and Science, Shibaura Institute of Technology, 307 Fukasaku, Minuma-ku, Saitama 337-8570, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gary J.","family":"Richards","sequence":"additional","affiliation":[{"name":"Graduate School of Engineering and Science, Shibaura Institute of Technology, 307 Fukasaku, Minuma-ku, Saitama 337-8570, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7964-1879","authenticated-orcid":false,"given":"Osamu","family":"Kitagawa","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry (Japanese Association of Bio-Intelligence for Well-Being), Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,11,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/B978-0-12-396530-1.00001-2","article-title":"Atropisomerism and Axial Chirality in Heteroaromatic Compounds","volume":"105","author":"Alkorta","year":"2012","journal-title":"Adv. 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