{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,23]],"date-time":"2026-04-23T11:20:45Z","timestamp":1776943245306,"version":"3.51.4"},"reference-count":29,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2007,3,29]],"date-time":"2007-03-29T00:00:00Z","timestamp":1175126400000},"content-version":"vor","delay-in-days":87,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["The Chemical Record"],"published-print":{"date-parts":[[2007,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Alk\u20102\u2010enyl(trialkyl)stannanes with heteroatom substituents at the 4\u2010, 5\u2010, and 6\u2010positions are transmetallated stereoselectively using tin(IV) halides to generate allyltin trihalides, which react with aldehydes to give (3<jats:italic>Z<\/jats:italic>)\u2010homoallylic alcohols with efficient 1,5\u2010, 1,6\u2010, and 1,7\u2010stereocontrol. This chemistry has been used to develop new strategies for natural product synthesis. Because of the toxicity of organotin reagents and the problems in removing organotin residues from reaction products, alternative procedures that avoid the use of organotin reagents have been investigated. To date, alk\u20102\u2010enylgermanium reagents have been shown to deliver effective 1,5\u2010 and 1,6\u2010stereocontrol, which is analogous to that observed for the organotin compounds. Organobismuth intermediates, which can be generated from allyl bromides and zinc\u2010bismuth(III)iodide, react with aldehydes with efficient 1,5\u2010stereocontrol which is complementary to that observed with the organo\u2010stannanes or \u2010germanes in that (3<jats:italic>E<\/jats:italic>)\u2010homoallylic alcohols are obtained. \u00a9 2007 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 7: 115\u2013124; 2007: Published online in Wiley InterScience (<jats:ext-link xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"http:\/\/www.interscience.wiley.com\">www.interscience.wiley.com<\/jats:ext-link>) DOI 10.1002\/tcr.20113<\/jats:p>","DOI":"10.1002\/tcr.20113","type":"journal-article","created":{"date-parts":[[2007,3,29]],"date-time":"2007-03-29T17:07:11Z","timestamp":1175188031000},"page":"115-124","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":34,"title":["Remote stereocontrol using functionalized allylmetal reagents"],"prefix":"10.1002","volume":"7","author":[{"given":"Eric J.","family":"Thomas","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2007,3,29]]},"reference":[{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00036-9"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/a603881f"},{"key":"e_1_2_7_4_2","first-page":"2383","volume":"691","author":"Nishigaichi Y.","year":"1996","journal-title":"Chem Lett"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)86867-9"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19890001521"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo9519975"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1994-25469"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)91625-3"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)79268-9"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39940000283"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1992-21424"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2005.11.042"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)00496-Y"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/a704293k"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/a800781k"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)02427-7"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)02428-9"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)01795-6"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)00921-2"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.3987\/COM-02-S56"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)01066-1"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)00358-4"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.11.065"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0295467"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/b303151a"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.63.1738"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.07.035"},{"key":"e_1_2_7_29_2","first-page":"2837","author":"Wang S.","year":"1999","journal-title":"J Chem Soc, Dalton Trans"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200250629"}],"container-title":["The Chemical Record"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Ftcr.20113","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/tcr.20113","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T04:35:08Z","timestamp":1697430908000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/tcr.20113"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2007,1]]},"references-count":29,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2007,1]]}},"alternative-id":["10.1002\/tcr.20113"],"URL":"https:\/\/doi.org\/10.1002\/tcr.20113","archive":["Portico"],"relation":{},"ISSN":["1527-8999","1528-0691"],"issn-type":[{"value":"1527-8999","type":"print"},{"value":"1528-0691","type":"electronic"}],"subject":[],"published":{"date-parts":[[2007,1]]},"assertion":[{"value":"2006-10-31","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2006-12-05","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2007-03-29","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}