{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T18:42:25Z","timestamp":1790707345088,"version":"4.1.0"},"reference-count":84,"publisher":"Wiley","issue":"42","license":[{"start":{"date-parts":[[2022,6,10]],"date-time":"2022-06-10T00:00:00Z","timestamp":1654819200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001700","name":"Ministry of Education, Culture, Sports, Science and Technology","doi-asserted-by":"publisher","award":["JP17H06447"],"award-info":[{"award-number":["JP17H06447"]}],"id":[{"id":"10.13039\/501100001700","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP16H06354"],"award-info":[{"award-number":["JP16H06354"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2022,7,26]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The formal enantioselective umpolung addition of dialkyl phosphites to 2\u2010azaaryl ketones was developed under Br\u00f8nsted base catalysis. The reaction involves the enantioselective protonation of the transient \u03b1\u2010oxygenated (2\u2010azaaryl)methyl anion generated through the 1,2\u2010addition of the anion of dialkyl phosphite to the 2\u2010azaaryl ketone and the subsequent [1,2]\u2010phospha\u2010Brook rearrangement. A chiral bis(guanidino)iminophosphorane organosuperbase efficiently catalyzed the reaction to provide enantio\u2010enriched phosphates in high yields with good to high enantioselectivities. This is a rare example of the catalytic enantioselective protonation of transient carbanions other than enolates, constructing a trisubstituted stereogenic center \u03b1 to 2\u2010azaarenes.<\/jats:p>","DOI":"10.1002\/chem.202201240","type":"journal-article","created":{"date-parts":[[2022,5,11]],"date-time":"2022-05-11T12:32:24Z","timestamp":1652272344000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Formal Umpolung Addition of Phosphites to 2\u2010Azaaryl Ketones under Chiral Br\u00f8nsted Base Catalysis: Enantioselective Protonation Utilizing [1,2]\u2010Phospha\u2010Brook Rearrangement"],"prefix":"10.1002","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7227-8579","authenticated-orcid":false,"given":"Azusa","family":"Kondoh","sequence":"first","affiliation":[{"name":"Research and Analytical Center for Giant Molecules Graduate School of Science Tohoku University Aramaki, Aoba-ku  Sendai 980-8578 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takayuki","family":"Hirozane","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Science Tohoku University Aramaki, Aoba-ku  Sendai 980-8578 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0554-8652","authenticated-orcid":false,"given":"Masahiro","family":"Terada","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Science Tohoku University Aramaki, Aoba-ku  Sendai 980-8578 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,6,10]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"For selected recent reviews on enantioselective protonation 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