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Catal."},{"key":"ref2\/cit2","unstructured":"For recent representative examples, see:"},{"key":"ref2\/cit2a","doi-asserted-by":"crossref","first-page":"1635","DOI":"10.1021\/ja973423i","volume":"120","author":"Imamoto T.","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"ref2\/cit2b","doi-asserted-by":"crossref","first-page":"1100","DOI":"10.1002\/(SICI)1521-3773(19980504)37:8<1100::AID-ANIE1100>3.0.CO;2-3","volume":"37","author":"Jiang Q.","year":"1998","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref2\/cit2c","doi-asserted-by":"crossref","first-page":"11539","DOI":"10.1021\/ja002507f","volume":"122","author":"van den Berg M.","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ref2\/cit2d","doi-asserted-by":"crossref","first-page":"3889","DOI":"10.1002\/1521-3773(20001103)39:21<3889::AID-ANIE3889>3.0.CO;2-T","volume":"39","author":"Reetz M. T.","year":"2000","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref2\/cit2e","doi-asserted-by":"crossref","first-page":"3425","DOI":"10.1002\/1521-3773(20010917)40:18<3425::AID-ANIE3425>3.0.CO;2-O","volume":"40","author":"Xiao D.","year":"2001","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref2\/cit2f","doi-asserted-by":"crossref","first-page":"1197","DOI":"10.1002\/1521-3773(20010401)40:7<1197::AID-ANIE1197>3.0.CO;2-G","volume":"40","author":"Komarov I. V.","year":"2001","journal-title":"Angew. Chem., Int. Ed"},{"key":"ref2\/cit2g","doi-asserted-by":"crossref","first-page":"1612","DOI":"10.1002\/1521-3773(20020503)41:9<1612::AID-ANIE1612>3.0.CO;2-H","volume":"41","author":"Tang W.","year":"2002","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref2\/cit2h","doi-asserted-by":"crossref","first-page":"612","DOI":"10.1002\/1521-3773(20020215)41:4<612::AID-ANIE612>3.0.CO;2-9","volume":"41","author":"Ostermeier M.","year":"2002","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref2\/cit2i","doi-asserted-by":"crossref","first-page":"2348","DOI":"10.1002\/1521-3773(20020703)41:13<2348::AID-ANIE2348>3.0.CO;2-K","volume":"41","author":"Hu A.-G.","year":"2002","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref2\/cit2j","doi-asserted-by":"crossref","first-page":"943","DOI":"10.1002\/anie.200390251","volume":"42","author":"Tang W.","year":"2003","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref2\/cit2k","doi-asserted-by":"crossref","first-page":"3509","DOI":"10.1002\/anie.200351465","volume":"42","author":"Tang W.","year":"2003","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref2\/cit2l","doi-asserted-by":"crossref","first-page":"3565","DOI":"10.1021\/ol048528m","volume":"6","author":"Wu S.","year":"2004","journal-title":"Org. Lett."},{"key":"ref2\/cit2n","doi-asserted-by":"crossref","first-page":"3585","DOI":"10.1021\/ol048519d","volume":"6","author":"Hu X.-P.","year":"2004","journal-title":"Org. 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Catal."},{"key":"ref5\/cit5a","doi-asserted-by":"crossref","first-page":"5966","DOI":"10.1021\/ja048496y","volume":"126","author":"Hoge G.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5b","doi-asserted-by":"crossref","first-page":"3645","DOI":"10.1021\/ol048386w","volume":"6","author":"Wu H.-P.","year":"2004","journal-title":"Org. Lett."},{"key":"ref5\/cit5c","doi-asserted-by":"crossref","first-page":"2560","DOI":"10.1021\/ja076542z","volume":"130","author":"Gridnev I. D.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref6\/cit6a","doi-asserted-by":"crossref","first-page":"4983","DOI":"10.1021\/om00011a006","volume":"14","author":"Marinetti A.","year":"1995","journal-title":"Organometallics"},{"key":"ref6\/cit6b","doi-asserted-by":"crossref","first-page":"81","DOI":"10.1039\/B309385A","author":"Calabr\u00f2 G.","year":"2004","journal-title":"Dalton Trans."},{"key":"ref6\/cit6c","doi-asserted-by":"crossref","first-page":"203","DOI":"10.1016\/S0022-328X(00)89056-7","volume":"221","author":"Payne N. C.","year":"1981","journal-title":"J. Organomet. Chem."},{"key":"ref7\/cit7","unstructured":"No bisphosphorus ligands containing a 1-oxy-1,1-bisphosphorus unit\n                      B\n                      can be found on SciFinder. An unconfirmed nonchiral structure containing 1-amino-1,1-bisphosphorus unit was recently reported, see:"},{"key":"ref7\/cit7a","doi-asserted-by":"crossref","first-page":"6900","DOI":"10.1021\/ic800430f","volume":"47","author":"Aluri B. R.","year":"2008","journal-title":"Inorg. Chem."},{"key":"ref8\/cit8","doi-asserted-by":"crossref","first-page":"176","DOI":"10.1021\/ol9025815","volume":"12","author":"Tang W.","year":"2010","journal-title":"Org. Lett."},{"key":"ref9\/cit9","doi-asserted-by":"crossref","first-page":"2788","DOI":"10.1021\/ja01038a065","volume":"91","author":"Naumann K.","year":"1969","journal-title":"J. Am. Chem. Soc."},{"key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"2017","DOI":"10.1016\/S0040-4039(00)93805-X","volume":"24","author":"Luckenbach R.","year":"1976","journal-title":"Tetrahedron Lett."},{"key":"ref11\/cit11","unstructured":"SeeSupporting Informationfor details."},{"key":"ref12\/cit12","unstructured":"Crystallographic data for compound Rh[(\n                      ent\n                      -\n                      3a\n                      )(nbd)]BF4 have been deposited at Cambridge Crystallographic Data Centre (deposition no. CCDC-760509). Copies of these data can be obtained free of charge viawww.ccdc.cam.ac.uk\/conts\/retrieving.html."},{"key":"ref13\/cit13","unstructured":"Enantioselectivities on hydrogenation of 2-acetamido-3-phenylacrylic acid (\n                      4a\n                      ) with the Rh catalysts of different ligands: 99% ee (\n                      3a\n                      ), 87% ee (\n                      3b\n                      ), 54% ee (\n                      3c\n                      ), and 92% ee (\n                      3d\n                      )."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"532","DOI":"10.1016\/j.ccr.2007.09.013","volume":"252","author":"Bruneau C.","year":"2008","journal-title":"Coord. Chem. Rev."},{"key":"ref14\/cit14a","doi-asserted-by":"crossref","first-page":"6329","DOI":"10.1016\/j.tetlet.2009.08.111","volume":"50","author":"Magano J.","year":"2009","journal-title":"Tetrahedron Lett."},{"key":"ref14\/cit14b","doi-asserted-by":"crossref","first-page":"355","DOI":"10.1021\/op034011z","volume":"7","author":"Drexler H.-J.","year":"2003","journal-title":"Org. Proc. Res. Dev."},{"key":"ref15\/cit15","unstructured":"Enantioselectivities on hydrogenation of (\n                      Z\n                      )-methyl 3-acetamidobut-2-enoate ((\n                      Z\n                      )-\n                      6a\n                      ) with the Rh catalysts of different ligands: 99% ee (\n                      3a\n                      ), 91% ee (\n                      3b\n                      ), 94% ee (\n                      3c\n                      ), and 75% ee (\n                      3d\n                      )."},{"key":"ref16\/cit16","unstructured":"Enantioselectivities on hydrogenation of (\n                      E\n                      )-methyl 3-acetamidobut-2-enoate ((\n                      E\n                      )-\n                      6a\n                      ) with the Rh catalysts of different ligands: 80% ee (\n                      3a\n                      ), 95% ee (\n                      3b\n                      ), 46% ee (\n                      3c\n                      ), and 88% ee (\n                      3d\n                      )."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol1000999","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,3,23]],"date-time":"2024-03-23T19:29:13Z","timestamp":1711222153000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol1000999"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,2,11]]},"references-count":48,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2010,3,5]]}},"alternative-id":["10.1021\/ol1000999"],"URL":"https:\/\/doi.org\/10.1021\/ol1000999","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2010,2,11]]}}}