{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,9]],"date-time":"2026-06-09T16:11:34Z","timestamp":1781021494581,"version":"3.54.1"},"reference-count":50,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2026,1,13]],"date-time":"2026-01-13T00:00:00Z","timestamp":1768262400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,1,13]],"date-time":"2026-01-13T00:00:00Z","timestamp":1768262400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100000038","name":"Natural Sciences and Engineering Research Council of Canada","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100000038","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2026,2,2]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    A novel stereospecific, transition\u2010metal\u2010free alkylation of cyanohydrins with enantiomerically enriched secondary tosylates is described. This method enables the general, efficient, and operationally simple synthesis of enantioenriched \u03b1\u2010tertiary ketones by leveraging the nucleophilicity of cyanohydrin anions, which serve as umpolung carbonyl equivalents to facilitate highly stereospecific S\n                    <jats:sub>N<\/jats:sub>\n                    2 substitutions. Reactions involving alkenyl cyanohydrins proceed through a stereoconvergent olefin synthesis (SCOS) from a geometric\n                    <jats:italic>E\/Z<\/jats:italic>\n                    mixture, furnishing stereochemically defined, conjugated \u03b1\u2010tertiary ketones. This methodology exhibits broad functional group tolerance, accommodating unactivated and sterically hindered acyclic and cyclic secondary tosylates. The resulting chiral ketones are configurationally stable and can be readily converted into synthetically versatile intermediates using classical transformations. The utility of this approach is exemplified by a concise, stereospecific synthesis of (\n                    <jats:italic>R<\/jats:italic>\n                    )\u2010cyclamen aldehyde, underscoring its potential to streamline the preparation of enantioenriched \u03b1\u2010tertiary ketones\u2014structural motifs that feature prominently in both natural and non\u2010natural products and serve as key intermediates in target\u2010directed synthesis.\n                  <\/jats:p>","DOI":"10.1002\/anie.202520674","type":"journal-article","created":{"date-parts":[[2026,1,14]],"date-time":"2026-01-14T07:36:21Z","timestamp":1768376181000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Stereospecific Transition\u2010Metal\u2010Free Alkylation of Chiral Non\u2010Racemic Secondary Tosylates with Cyanohydrins: Convenient Access to Enantiomerically Enriched \u03b1\u2010Tertiary Ketones"],"prefix":"10.1002","volume":"65","author":[{"ORCID":"https:\/\/orcid.org\/0009-0000-3617-5935","authenticated-orcid":false,"given":"Jinjin","family":"Ma","sequence":"first","affiliation":[{"name":"Department of Chemistry Queen's University  90 Bader Lane Kingston K7L 3N6 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hui","family":"Li","sequence":"additional","affiliation":[{"name":"Department of Chemistry Queen's University  90 Bader Lane Kingston K7L 3N6 Canada"},{"name":"College of Chemistry &amp; Pharmacy Northwest A&amp;F University  Yangling Shaanxi 712100 P. R. of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8600-304X","authenticated-orcid":false,"given":"Jadab","family":"Majhi","sequence":"additional","affiliation":[{"name":"Department of Chemistry Queen's University  90 Bader Lane Kingston K7L 3N6 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6609-5282","authenticated-orcid":false,"given":"P. Andrew","family":"Evans","sequence":"additional","affiliation":[{"name":"Department of Chemistry Queen's University  90 Bader Lane Kingston K7L 3N6 Canada"},{"name":"Xiangya School of Pharmaceutical Sciences Central South University  Changsha Hunan 410013 P. R. of China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,1,13]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biopha.2008.08.024"},{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.53.591"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-013-5335-6"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201400241"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00381"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00564"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201703079"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.6023\/cjoc202211045"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja909689t"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c09807"},{"key":"e_1_2_6_11_1","first-page":"327","volume-title":"Mechanism and Theory in Organic Chemistry","author":"Lowry T. 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