{"corpus_id":32435916,"paper_sha":"ccc4e829b1bd5cae508345d6dae7814ffd52607d","doi":"10.1039/c5ob02617b","arxiv_id":null,"pmid":26846582,"pmcid":null,"mag_id":2266466963,"dblp_id":null,"acl_id":null,"title":"Chemoselective and stereoselective lithium carbenoid mediated cyclopropanation of acyclic allylic alcohols.","year":2016,"publication_date":"2016-02-24","venue":"Organic and biomolecular chemistry","journal":{"name":"Organic & biomolecular chemistry","pages":"\n          2731-41\n        ","volume":"14 9"},"journal_issn":null,"journal_title":null,"publication_types":["JournalArticle"],"pubmed_pub_types":["Journal Article","Research Support, Non-U.S. Gov't"],"s2_fields_of_study":["Medicine","Chemistry"],"reference_count":88,"citation_count":12,"influential_citation_count":0,"is_open_access":true,"arxiv_categories":null,"arxiv_license":null,"arxiv_journal_ref":null,"mesh_headings":[{"d":"Cyclopropanes","mj":false,"qs":[{"q":"chemical synthesis","mj":true,"ui":"Q000138"},{"q":"chemistry","mj":false,"ui":"Q000737"}],"ui":"D003521"},{"d":"Lithium","mj":false,"qs":[{"q":"chemistry","mj":true,"ui":"Q000737"}],"ui":"D008094"},{"d":"Methane","mj":false,"qs":[{"q":"analogs & derivatives","mj":true,"ui":"Q000031"},{"q":"chemistry","mj":false,"ui":"Q000737"}],"ui":"D008697"},{"d":"Molecular Structure","mj":false,"ui":"D015394"},{"d":"Propanols","mj":false,"qs":[{"q":"chemistry","mj":true,"ui":"Q000737"}],"ui":"D020005"},{"d":"Stereoisomerism","mj":false,"ui":"D013237"}],"chemicals":[{"n":"Cyclopropanes","ui":"D003521","reg":"0"},{"n":"Propanols","ui":"D020005","reg":"0"},{"n":"carbene","ui":"C030011","reg":"2465-56-7"},{"n":"allyl alcohol","ui":"C006463","reg":"3W678R12M0"},{"n":"Lithium","ui":"D008094","reg":"9FN79X2M3F"},{"n":"Methane","ui":"D008697","reg":"OP0UW79H66"}],"comments_corrections":null,"source_flags":5,"s2_open_access_pdf_url":"https://rodin.uca.es/bitstream/10498/20593/1/2016-Chemoselective%20and%20stereoselective%20lithium%20carbenoid%20mediated%20cyclopropanation%20of%20acyclic%20allylic%20alcohols.pdf","s2_open_access_landing_url":"https://www.semanticscholar.org/paper/ccc4e829b1bd5cae508345d6dae7814ffd52607d","s2_open_access_license":"CCBYNCND","s2_open_access_status":"GREEN","pmc_open_access_pdf_url":null,"pmc_open_access_landing_url":null,"pmc_open_access_license":null,"pmc_open_access_status":null,"unpaywall_open_access_pdf_url":null,"unpaywall_open_access_landing_url":null,"unpaywall_open_access_license":null,"unpaywall_open_access_status":null,"abstract":"The reaction of geraniol with different lithium carbenoids generated from n-BuLi and the corresponding dihaloalkane has been evaluated. The reaction occurs in a chemo and stereoselective manner, which is consistent with a directing effect from the oxygen of the allylic moiety. Furthermore, a set of polyenes containing allylic hydroxyl or ether groups were chemoselectively and stereoselectively converted into the corresponding gem-dimethylcyclopropanes in one single step in moderate to good yields mediated by a lithium carbenoid generated in situ by the reaction of n-BuLi and 2,2-dibromopropane.","claims":[{"public_id":"cl_238c1e1fbf36fbfa19d172a3c505728c","status":"active","text":"A lithium carbenoid generated in situ from n-BuLi and 2,2-dibromopropane mediates the chemoselective and stereoselective cyclopropanation of these substrates.","confidence":0.94,"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/claims/cl_238c1e1fbf36fbfa19d172a3c505728c"},{"public_id":"cl_68692831bb4a672add3738f81ac299f7","status":"active","text":"Geraniol reacts with lithium carbenoids in a chemo- and stereoselective manner, consistent with 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