{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T03:51:28Z","timestamp":1790826688995,"version":"4.1.0"},"reference-count":108,"publisher":"Wiley","issue":"37","license":[{"start":{"date-parts":[[2020,7,16]],"date-time":"2020-07-16T00:00:00Z","timestamp":1594857600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["GM094541"],"award-info":[{"award-number":["GM094541"]}],"id":[{"id":"10.13039\/100000057","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":[[2020,9,7]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The first\n                    <jats:italic>trans<\/jats:italic>\n                    \u2010selective cyanoboration reaction of an alkyne, specifically a 1,3\u2010enyne, is described. The reported palladium\u2010catalyzed cyanoboration of 1,3\u2010enynes is site\u2010, regio\u2010, and diastereoselective, and is uniquely enabled by the 1,4\u2010azaborine\u2010based Senphos ligand structure. Tetra\u2010substituted alkenyl nitriles are obtained providing useful boron\u2010dienenitrile building blocks that can be further functionalized. The utility of our method has been demonstrated with the synthesis of Satigrel, an anti\u2010platelet aggregating agent.\n                  <\/jats:p>","DOI":"10.1002\/anie.202005882","type":"journal-article","created":{"date-parts":[[2020,6,8]],"date-time":"2020-06-08T15:43:45Z","timestamp":1591631025000},"page":"15928-15932","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":57,"title":["Pd\u2010Senphos Catalyzed\n                    <i>trans<\/i>\n                    \u2010Selective Cyanoboration of 1,3\u2010Enynes"],"prefix":"10.1002","volume":"59","author":[{"given":"Yuanzhe","family":"Zhang","sequence":"first","affiliation":[{"name":"Department of Chemistry Boston College  Chestnut Hill MA 02467-3860 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bo","family":"Li","sequence":"additional","affiliation":[{"name":"Department of Chemistry Boston College  Chestnut Hill MA 02467-3860 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3148-9147","authenticated-orcid":false,"given":"Shih\u2010Yuan","family":"Liu","sequence":"additional","affiliation":[{"name":"Department of Chemistry Boston College  Chestnut Hill MA 02467-3860 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,7,16]]},"reference":[{"key":"e_1_2_2_1_1","volume-title":"Ullmann's Encyclopedia of Industrial Chemistry","author":"Brazdil J. 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For the synthesis of the related 2-cyano-2 3-dihydro-1 3-dimethyl-1H-1 3 2-benzodiazabolole see reference\u2005[14]."},{"key":"e_1_2_2_84_1","unstructured":"Under the optimized conditions about 1\u2009% of chloroboration of substrate1\u2009awas observed in 78:22trans:cisratio."},{"key":"e_1_2_2_85_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja067975p"},{"key":"e_1_2_2_86_1","unstructured":"When the reaction was performed withL1as the ligand the product4\u2009lwas obtained in 81\u2009% yield 94:6 (trans\/cis)ratio."},{"key":"e_1_2_2_87_1","unstructured":"When the reaction was performed with2\u2009fas the substrate andL1as the ligand the product5\u2009fwas obtained in 46\u2009% yield with (91:9)trans\/cisratio."},{"key":"e_1_2_2_88_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol901113t"},{"key":"e_1_2_2_89_1","unstructured":"\u00a0"},{"key":"e_1_2_2_90_2","first-page":"1143","volume":"37","author":"Fujimori T.","year":"1987","journal-title":"Arzneim.-Forsch."},{"key":"e_1_2_2_91_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.275.2.883"},{"key":"e_1_2_2_92_2","doi-asserted-by":"publisher","DOI":"10.1006\/bbrc.1994.2307"},{"key":"e_1_2_2_93_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1527-3466.1991.tb00416.x"},{"key":"e_1_2_2_94_1","unstructured":"\u00a0"},{"key":"e_1_2_2_95_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2015.06.024"},{"key":"e_1_2_2_96_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397910600764121"},{"key":"e_1_2_2_97_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00354a037"},{"key":"e_1_2_2_98_1","doi-asserted-by":"publisher","DOI":"10.1139\/v11-116"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.202005882","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202005882","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202005882","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202005882","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,3,28]],"date-time":"2024-03-28T10:50:56Z","timestamp":1711623056000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202005882"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,7,16]]},"references-count":108,"journal-issue":{"issue":"37","published-print":{"date-parts":[[2020,9,7]]}},"alternative-id":["10.1002\/anie.202005882"],"URL":"https:\/\/doi.org\/10.1002\/anie.202005882","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,7,16]]},"assertion":[{"value":"2020-04-23","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-07-16","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}