{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,7]],"date-time":"2026-09-07T17:10:19Z","timestamp":1788801019989,"version":"build-2803163510"},"reference-count":28,"publisher":"American Chemical Society (ACS)","issue":"2","license":[{"start":{"date-parts":[[2015,1,5]],"date-time":"2015-01-05T00:00:00Z","timestamp":1420416000000},"content-version":"vor","delay-in-days":17,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_ccby_termsofuse.html"}],"funder":[{"DOI":"10.13039\/501100002428","name":"Austrian Science Fund","doi-asserted-by":"publisher","award":["P19869-N19"],"award-info":[{"award-number":["P19869-N19"]}],"id":[{"id":"10.13039\/501100002428","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2015,1,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>LiTMP metalated dimethyl N-Boc-phosphoramidates derived from 1-phenylethylamine and 1,2,3,4-tetrahydronaphthalen-1-ylamine highly selectively at the CH3O group to generate short-lived oxymethyllithiums. These isomerized to diastereomeric hydroxymethylphosphonamidates (phosphate\u2013phosphonate rearrangement). However, s-BuLi converted the dimethyl N-Boc-phosphoramidate derived from 1-phenylethylamine to the N-Boc \u03b1-aminophosphonate preferentially. Only s-BuLi deprotonated dimethyl hydroxymethylphosphonamidates at the benzylic position and dimethyl N-Boc \u03b1-aminophosphonates at the CH3O group to induce phosphonate\u2013phosphinate rearrangements. In the former case, the migration of the phosphorus substituent from the nitrogen to the carbon atom followed a retentive course with some racemization because of the involvement of a benzyllithium as an intermediate.<\/jats:p>","DOI":"10.1021\/jo502567j","type":"journal-article","created":{"date-parts":[[2014,12,19]],"date-time":"2014-12-19T18:54:46Z","timestamp":1419015286000},"page":"1082-1091","source":"Crossref","is-referenced-by-count":9,"title":["Phosphonate\u2013Phosphinate\nRearrangement"],"prefix":"10.1021","volume":"80","author":[{"given":"Renzhe","family":"Qian","sequence":"first","affiliation":[{"name":"University of Vienna , , Wa\u0308hringerstrasse 38 , ,","place":["Vienna, Austria, A-1090"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander","family":"Roller","sequence":"additional","affiliation":[{"name":"University of Vienna , , Wa\u0308hringerstrasse 42 , ,","place":["Vienna, Austria, A-1090"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Friedrich","family":"Hammerschmidt","sequence":"additional","affiliation":[{"name":"University of Vienna , , Wa\u0308hringerstrasse 38 , ,","place":["Vienna, Austria, A-1090"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2014,12,19]]},"reference":[{"issue":"Se\u0301rie C","key":"2026090314112785400_cit1a","first-page":"1807","volume":"276","author":"Sturtz","year":"1973","journal-title":"C. R. Acad. Sci. Paris"},{"key":"2026090314112785400_cit1b","doi-asserted-by":"crossref","first-page":"13109","DOI":"10.1016\/S0040-4020(99)00822-4","volume":"55","author":"Eymery","year":"1999","journal-title":"Tetrahedron"},{"key":"2026090314112785400_cit2","doi-asserted-by":"crossref","first-page":"2239","DOI":"10.1002\/1099-0690(200006)2000:12<2239::AID-EJOC2239>3.0.CO;2-V","author":"Hammerschmidt","year":"2000","journal-title":"Eur. J. Org. Chem."},{"key":"2026090314112785400_cit3","doi-asserted-by":"crossref","first-page":"5220","DOI":"10.1039\/c1ob05246b","volume":"9","author":"Philippitsch","year":"2011","journal-title":"Org. Biomol. Chem."},{"key":"2026090314112785400_cit4","first-page":"8603","volume":"14","author":"Kuliszewska","year":"2008","journal-title":"Chem.\u2500Eur.\nJ."},{"key":"2026090314112785400_cit5","first-page":"19","volume":"2","author":"Brienne","year":"1978","journal-title":"Nouv. J. Chim."},{"key":"2026090314112785400_cit6","doi-asserted-by":"crossref","first-page":"989","DOI":"10.1351\/pac198052040989","volume":"52","author":"Pudovik","year":"1980","journal-title":"Pure Appl. Chem."},{"key":"2026090314112785400_cit7","doi-asserted-by":"crossref","first-page":"1063","DOI":"10.1007\/BF00814152","volume":"124","author":"Hammerschmidt","year":"1993","journal-title":"Monatsh. Chem."},{"key":"2026090314112785400_cit8a","doi-asserted-by":"crossref","first-page":"1854","DOI":"10.1002\/ange.19931051246","volume":"105","author":"Meier","year":"1993","journal-title":"Angew. Chem."},{"key":"2026090314112785400_cit8a1","doi-asserted-by":"crossref","first-page":"1704","DOI":"10.1002\/anie.199317041","volume":"32","author":"Meier","year":"1993","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"2026090314112785400_cit9","first-page":"123","volume-title":"Houben-Weyl\u2500Methoden\nder Organischen Chemie, E2\nPhosphorverbindungen II","author":"Felcht","year":"1982"},{"key":"2026090314112785400_cit10a","volume-title":"Aminophosphonic and\nAminophosphinic Acids, Chemistry and Biological Activity","author":"Kukhar","year":"2000"},{"key":"2026090314112785400_cit10b","doi-asserted-by":"crossref","first-page":"3404","DOI":"10.1021\/ol3013793","volume":"14","author":"Berger","year":"2012","journal-title":"Org. Lett."},{"key":"2026090314112785400_cit11a","doi-asserted-by":"crossref","first-page":"5591","DOI":"10.1016\/S0040-4039(00)97904-8","volume":"31","author":"Patel","year":"1990","journal-title":"Tetrahedron Lett."},{"issue":"Suppl. 10","key":"2026090314112785400_cit11b","first-page":"S7","volume":"20","author":"Weber","year":"1992","journal-title":"J. Cardiovasc. Pharmacol."},{"key":"2026090314112785400_cit11c","doi-asserted-by":"crossref","first-page":"6625","DOI":"10.1016\/S0040-4039(00)61002-X","volume":"33","author":"Stowasser","year":"1992","journal-title":"Tetrahedron Lett."},{"key":"2026090314112785400_cit11d","doi-asserted-by":"crossref","first-page":"12059","DOI":"10.1021\/ja00105a059","volume":"116","author":"Hiratake","year":"1994","journal-title":"J.\nAm. Chem. Soc."},{"key":"2026090314112785400_cit11e","doi-asserted-by":"crossref","first-page":"158","DOI":"10.1021\/jm00027a020","volume":"37","author":"Bird","year":"1994","journal-title":"J. Med. Chem."},{"key":"2026090314112785400_cit11f","doi-asserted-by":"crossref","first-page":"4557","DOI":"10.1021\/jm00022a022","volume":"38","author":"Patel","year":"1995","journal-title":"J. Med. Chem."},{"key":"2026090314112785400_cit12","doi-asserted-by":"crossref","first-page":"883","DOI":"10.1070\/RC2011v080n09ABEH004165","volume":"80","author":"Kolodiazhnyi","year":"2011","journal-title":"Russ. Chem. Rev."},{"key":"2026090314112785400_cit13","doi-asserted-by":"crossref","first-page":"277","DOI":"10.1002\/0471698482.ch13","volume-title":"Enantioselective Synthesis\nof \u03b1-Amino Acids","author":"Palacios","year":"2005","edition":"2"},{"key":"2026090314112785400_cit14","doi-asserted-by":"crossref","first-page":"589","DOI":"10.1039\/a809398i","volume":"16","author":"Seto","year":"1999","journal-title":"Nat. Prod. Rep."},{"key":"2026090314112785400_cit15","first-page":"303","volume-title":"Modern Crop Protection\nCompounds","author":"Donn","year":"2007"},{"key":"2026090314112785400_cit16","doi-asserted-by":"crossref","first-page":"331","DOI":"10.1016\/S0040-4039(00)84010-1","volume":"27","author":"Fraser","year":"1986","journal-title":"Tetrahedron Lett."},{"key":"2026090314112785400_cit17","doi-asserted-by":"crossref","first-page":"1079","DOI":"10.1016\/S0040-4039(01)02289-4","volume":"43","author":"Klepacz","year":"2002","journal-title":"Tetrahedron Lett."},{"key":"2026090314112785400_cit18","first-page":"5729","volume":"15","author":"D. C. Kapeller","year":"2009","journal-title":"Chem.\u2500Eur. J."},{"key":"2026090314112785400_cit19","doi-asserted-by":"crossref","first-page":"471","DOI":"10.1021\/cr00063a003","volume":"84","author":"Beak","year":"1984","journal-title":"Chem. Rev."},{"key":"2026090314112785400_cit20","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1016\/0924-2031(92)85011-O","volume":"3","author":"Mikenda","year":"1992","journal-title":"Vib. Spectrosc."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo502567j","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/80\/2\/1082\/13817158\/jo502567j.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/80\/2\/1082\/13817158\/jo502567j.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,7]],"date-time":"2026-09-07T17:03:22Z","timestamp":1788800602000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/joceah\/article\/80\/2\/1082\/1350101\/Phosphonate-Phosphinate-Rearrangement"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,12,19]]},"references-count":28,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2014,12,19]]},"published-print":{"date-parts":[[2015,1,16]]}},"URL":"https:\/\/doi.org\/10.1021\/jo502567j","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,12,19]]}}}