{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T03:33:07Z","timestamp":1791084787352,"version":"4.1.0"},"reference-count":59,"publisher":"American Chemical Society (ACS)","issue":"38","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Am. Chem. Soc."],"published-print":{"date-parts":[[2005,9,28]]},"DOI":"10.1021\/ja0539443","type":"journal-article","created":{"date-parts":[[2005,9,21]],"date-time":"2005-09-21T05:11:16Z","timestamp":1127279476000},"page":"13386-13398","source":"Crossref","is-referenced-by-count":103,"title":["Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to Methacrolein Catalyzed by (\u03b7<sup>5<\/sup>-C<sub>5<\/sub>Me<sub>5<\/sub>)M{(<i>R<\/i>)-Prophos} Containing Complexes (M = Rh, Ir; (<i>R<\/i>)-Prophos = 1,2-bis(Diphenylphosphino)propane):\u2009 On the Origin of the Enantioselectivity"],"prefix":"10.1021","volume":"127","author":[{"given":"Daniel","family":"Carmona","sequence":"first","affiliation":[{"name":"Contribution from the Departamento de Qu\u00edmica Inorg\u00e1nica and Departamento de Qu\u00edmica Org\u00e1nica, Instituto Universitario de Cat\u00e1lisis Homog\u00e9nea, Instituto de Ciencia de Materiales de Arag\u00f3n, Universidad de Zaragoza-Consejo Superior de Investigaciones Cient\u00edficas, 50009 Zaragoza, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"M. Pilar","family":"Lamata","sequence":"additional","affiliation":[{"name":"Contribution from the Departamento de Qu\u00edmica Inorg\u00e1nica and Departamento de Qu\u00edmica Org\u00e1nica, Instituto Universitario de Cat\u00e1lisis Homog\u00e9nea, Instituto de Ciencia de Materiales de Arag\u00f3n, Universidad de Zaragoza-Consejo Superior de Investigaciones Cient\u00edficas, 50009 Zaragoza, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fernando","family":"Viguri","sequence":"additional","affiliation":[{"name":"Contribution from the Departamento de Qu\u00edmica Inorg\u00e1nica and Departamento de Qu\u00edmica Org\u00e1nica, Instituto Universitario de Cat\u00e1lisis Homog\u00e9nea, Instituto de Ciencia de Materiales de Arag\u00f3n, Universidad de Zaragoza-Consejo Superior de Investigaciones Cient\u00edficas, 50009 Zaragoza, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ricardo","family":"Rodr\u00edguez","sequence":"additional","affiliation":[{"name":"Contribution from the Departamento de Qu\u00edmica Inorg\u00e1nica and Departamento de Qu\u00edmica Org\u00e1nica, Instituto Universitario de Cat\u00e1lisis Homog\u00e9nea, Instituto de Ciencia de Materiales de Arag\u00f3n, Universidad de Zaragoza-Consejo Superior de Investigaciones Cient\u00edficas, 50009 Zaragoza, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luis A.","family":"Oro","sequence":"additional","affiliation":[{"name":"Contribution from the Departamento de Qu\u00edmica Inorg\u00e1nica and Departamento de Qu\u00edmica Org\u00e1nica, Instituto Universitario de Cat\u00e1lisis Homog\u00e9nea, Instituto de Ciencia de Materiales de Arag\u00f3n, Universidad de Zaragoza-Consejo Superior de Investigaciones Cient\u00edficas, 50009 Zaragoza, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fernando J.","family":"Lahoz","sequence":"additional","affiliation":[{"name":"Contribution from the Departamento de Qu\u00edmica Inorg\u00e1nica and Departamento de Qu\u00edmica Org\u00e1nica, Instituto Universitario de Cat\u00e1lisis Homog\u00e9nea, Instituto de Ciencia de Materiales de Arag\u00f3n, Universidad de Zaragoza-Consejo Superior de Investigaciones Cient\u00edficas, 50009 Zaragoza, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ana I.","family":"Balana","sequence":"additional","affiliation":[{"name":"Contribution from the Departamento de Qu\u00edmica Inorg\u00e1nica and Departamento de Qu\u00edmica Org\u00e1nica, Instituto Universitario de Cat\u00e1lisis Homog\u00e9nea, Instituto de Ciencia de Materiales de Arag\u00f3n, Universidad de Zaragoza-Consejo Superior de Investigaciones Cient\u00edficas, 50009 Zaragoza, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tom\u00e1s","family":"Tejero","sequence":"additional","affiliation":[{"name":"Contribution from the Departamento de Qu\u00edmica Inorg\u00e1nica and Departamento de Qu\u00edmica Org\u00e1nica, Instituto Universitario de Cat\u00e1lisis Homog\u00e9nea, Instituto de Ciencia de Materiales de Arag\u00f3n, Universidad de Zaragoza-Consejo Superior de Investigaciones Cient\u00edficas, 50009 Zaragoza, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pedro","family":"Merino","sequence":"additional","affiliation":[{"name":"Contribution from the Departamento de Qu\u00edmica Inorg\u00e1nica and Departamento de Qu\u00edmica Org\u00e1nica, Instituto Universitario de Cat\u00e1lisis Homog\u00e9nea, Instituto de Ciencia de Materiales de Arag\u00f3n, Universidad de Zaragoza-Consejo Superior de Investigaciones Cient\u00edficas, 50009 Zaragoza, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2005,8,31]]},"reference":[{"key":"ja0539443b00001\/ja0539443b00001_1","volume-title":"Springer:\u2009 New York","author":"Comprehensive Asymmetric Catalysis","year":"1999"},{"key":"ja0539443b00001\/ja0539443b00001_2","unstructured":"(b)Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH:\u2009 Weinheim, Germany, 2000."},{"key":"ja0539443b00001\/ja0539443b00001_3","volume-title":"Asymmetric Catalysis in Organic Synthesis","author":"Noyori R.","year":"1994"},{"key":"ja0539443b00002\/ja0539443b00002_1","volume-title":"Wiley-VCH:\u2009 Weinheim","author":"Cycloaddition Reactions","year":"2002"},{"key":"ja0539443b00003\/ja0539443b00003_1","volume-title":"New Jersey","year":"2003"},{"key":"ja0539443b00003\/ja0539443b00003_2","first-page":"425","volume":"53","author":"Frederickson M.","year":"1997","journal-title":"Tetrahedron"},{"key":"ja0539443b00004\/ja0539443b00004_1","doi-asserted-by":"crossref","first-page":"1019","DOI":"10.1021\/cr00013a013","volume":"92","author":"Kagan H. B.","year":"1992","journal-title":"Chem. Rev."},{"key":"ja0539443b00004\/ja0539443b00004_2","first-page":"332","volume":"8","author":"Dias L. C.","year":"1997","journal-title":"J. Braz. Chem. Soc."},{"key":"ja0539443b00004\/ja0539443b00004_3","unstructured":"(c) Evans, D. A.; Johnson, J. S. InComprehensive Asymmetric Catalysis, Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds; Springer:\u2009 New York, 1999; Vol II, Chapter 33.1, pp 1178\u22121235."},{"key":"ja0539443b00004\/ja0539443b00004_4","first-page":"772","volume":"200","author":"Carmona D.","year":"2000","journal-title":"Coord. Chem. Rev."},{"key":"ja0539443b00005\/ja0539443b00005_1","volume-title":"In 1,3-Dipolar Cycloaddition Chemistry","author":"Tufariello J. J.","year":"1984"},{"key":"ja0539443b00006\/ja0539443b00006_1","doi-asserted-by":"crossref","first-page":"909","DOI":"10.1021\/cr970324e","volume":"98","author":"Gothelf K. V.","year":"1998","journal-title":"Chem. Rev."},{"key":"ja0539443b00006\/ja0539443b00006_2","first-page":"1458","volume":"1449","author":"Gothelf K. V.","year":"2000","journal-title":"Chem. Commun."},{"key":"ja0539443b00007\/ja0539443b00007_1","doi-asserted-by":"crossref","first-page":"4969","DOI":"10.1021\/ja017814f","volume":"124","author":"Viton F.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ja0539443b00008\/ja0539443b00008_1","first-page":"2460","volume":"4","author":"Mita T.","year":"2002","journal-title":"Org. Lett."},{"key":"ja0539443b00008\/ja0539443b00008_2","first-page":"1466","volume":"1462","author":"Ohtsuki N.","year":"2003","journal-title":"Synthesis"},{"key":"ja0539443b00008\/ja0539443b00008_3","first-page":"2207","volume":"76","author":"Kezuka S.","year":"2003","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ja0539443b00009\/ja0539443b00009_1","doi-asserted-by":"crossref","first-page":"678","DOI":"10.1021\/ol0361148","volume":"6","author":"Shirahase M.","year":"2004","journal-title":"Org. Lett."},{"key":"ja0539443b00010\/ja0539443b00010_1","doi-asserted-by":"crossref","first-page":"1223","DOI":"10.1002\/(SICI)1521-3773(19990503)38:9<1219::AID-ANIE1219>3.0.CO;2-D","volume":"38","author":"K\u00fcndig E. P.","year":"1999","journal-title":"Angew. Chem., Int. Ed."},{"key":"ja0539443b00011\/ja0539443b00011_1","first-page":"2352","volume":"2351","author":"Carmona D.","year":"1997","journal-title":"Chem. Commun."},{"key":"ja0539443b00012\/ja0539443b00012_1","first-page":"1248","volume":"1247","author":"Carmona D.","year":"1996","journal-title":"Chem. Commun."},{"key":"ja0539443b00013\/ja0539443b00013_1","first-page":"2717","volume":"126","author":"For","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ja0539443b00014\/ja0539443b00014_1","first-page":"1661","volume":"1654","author":"White C.","year":"1977","journal-title":"J. Chem. Soc., Dalton Trans."},{"key":"ja0539443b00015\/ja0539443b00015_1","doi-asserted-by":"crossref","first-page":"800","DOI":"10.1002\/anie.199507981","volume":"34","author":"Evans D. A.","year":"1995","journal-title":"J. Angew. Chem., Int. Ed. Engl."},{"key":"ja0539443b00016\/ja0539443b00016_1","first-page":"415","volume":"5","author":"Cahn R. S.","year":"1966","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ja0539443b00016\/ja0539443b00016_2","doi-asserted-by":"crossref","first-page":"583","DOI":"10.1002\/anie.198205671","volume":"21","author":"Prelog V.","year":"1982","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ja0539443b00016\/ja0539443b00016_3","doi-asserted-by":"crossref","first-page":"76","DOI":"10.1016\/S0022-328X(00)80382-4","volume":"73","author":"Lecomte C.","year":"1974","journal-title":"J. Organomet. Chem."},{"key":"ja0539443b00016\/ja0539443b00016_4","doi-asserted-by":"crossref","first-page":"6599","DOI":"10.1021\/ja00855a064","volume":"97","author":"Stanley K.","year":"1975","journal-title":"J. Am. Chem. Soc."},{"key":"ja0539443b00016\/ja0539443b00016_5","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/9780470147214.ch1","volume":"12","author":"Sloan T. E.","year":"1981","journal-title":"Top. Stereochem."},{"key":"ja0539443b00017\/ja0539443b00017_1","volume-title":"Blackwell:\u2009 Oxford","author":"Nomenclature","year":"1991"},{"key":"ja0539443b00020\/ja0539443b00020_1","doi-asserted-by":"crossref","first-page":"1358","DOI":"10.1021\/ja00839a012","volume":"97","author":"Cremer D.","year":"1975","journal-title":"J. Am. Chem. Soc."},{"key":"ja0539443b00021\/ja0539443b00021_1","first-page":"S19","volume":"1","author":"Allen F. H.","year":"1987","journal-title":"J. Chem. Soc., Perkin Trans."},{"key":"ja0539443b00023\/ja0539443b00023_1","first-page":"3155","volume":"3148","author":"Suezawa H.","year":"2002","journal-title":"Eur. J. Inorg. Chem."},{"key":"ja0539443b00023\/ja0539443b00023_2","doi-asserted-by":"crossref","first-page":"1213","DOI":"10.1246\/bcsj.71.1207","volume":"71","author":"Umezawa Y.","year":"1998","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ja0539443b00024\/ja0539443b00024_1","first-page":"2251","volume":"53","author":"Okawa H.","year":"1980","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ja0539443b00024\/ja0539443b00024_2","doi-asserted-by":"crossref","first-page":"1598","DOI":"10.1021\/ic00134a064","volume":"21","author":"Okawa H.","year":"1982","journal-title":"Inorg. Chem."},{"key":"ja0539443b00025\/ja0539443b00025_1","doi-asserted-by":"crossref","first-page":"1208","DOI":"10.1002\/(SICI)1521-3773(19990503)38:9<1194::AID-ANIE1194>3.0.CO;2-X","volume":"38","author":"Brunner H.","year":"1999","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ja0539443b00025\/ja0539443b00025_2","first-page":"1508","volume":"1499","author":"Brunner H.","year":"1996","journal-title":"J. Chem. Soc., Dalton Trans."},{"key":"ja0539443b00025\/ja0539443b00025_3","doi-asserted-by":"crossref","first-page":"1012","DOI":"10.1002\/anie.198310121","volume":"22","author":"Brunner H.","year":"1983","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ja0539443b00026\/ja0539443b00026_1","doi-asserted-by":"crossref","first-page":"2821","DOI":"10.1002\/1521-3773(20010803)40:15<2818::AID-ANIE2818>3.0.CO;2-Y","volume":"40","author":"Yamakawa M.","year":"2001","journal-title":"Angew. Chem., Int. Ed."},{"key":"ja0539443b00026\/ja0539443b00026_2","doi-asserted-by":"crossref","first-page":"1478","DOI":"10.1021\/ja991638h","volume":"122","author":"Yamakawa M.","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ja0539443b00027\/ja0539443b00027_1","doi-asserted-by":"crossref","first-page":"158","DOI":"10.1039\/b313104a","volume":"6","author":"Nishio M.","year":"2004","journal-title":"CrystEngComm."},{"key":"ja0539443b00027\/ja0539443b00027_2","volume-title":"The CH\/\u03c0 Interaction. Evidence, Nature, and Consequences","author":"Nishio M.","year":"1998"},{"key":"ja0539443b00030\/ja0539443b00030_1","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1021\/ic50071a029","volume":"8","author":"Hutchison J. R.","year":"1969","journal-title":"Inorg. Chem."},{"key":"ja0539443b00030\/ja0539443b00030_2","doi-asserted-by":"crossref","first-page":"349","DOI":"10.1007\/BF00618348","volume":"7","author":"Sivasubramanian S.","year":"1982","journal-title":"Transition Met. Chem."},{"key":"ja0539443b00030\/ja0539443b00030_3","doi-asserted-by":"crossref","unstructured":"(c) Das, P.; Boruah, M.; Kumari, N.; Sharma, M.; Konwar, D.; Dutta, D. K.J.Mol. Catal. A:\u2009Chem.2002,178, 283\u2212287.","DOI":"10.1016\/S1381-1169(01)00338-7"},{"key":"ja0539443b00031\/ja0539443b00031_1","first-page":"1453","volume":"37","author":"Villamena F. A.","year":"1998","journal-title":"Inorg. Chem."},{"key":"ja0539443b00031\/ja0539443b00031_3","first-page":"2342","volume":"2336","author":"Merino P.","year":"2003","journal-title":"Org. Biomol. Chem."},{"key":"ja0539443b00031\/ja0539443b00031_4","first-page":"1795","volume":"689","author":"Ade A.","year":"2004","journal-title":"J. Organomet. Chem."},{"key":"ja0539443b00032\/ja0539443b00032_1","first-page":"381","volume":"380","author":"Lee J.","year":"2002","journal-title":"Chem. Commun."},{"key":"ja0539443b00035\/ja0539443b00035_1","first-page":"905","volume":"57","author":"Tanaka J.","year":"2001","journal-title":"Tetrahedron"},{"key":"ja0539443b00036\/ja0539443b00036_1","first-page":"5920","volume":"44","author":"Ali S. A.","year":"1988","journal-title":"Tetrahedron"},{"key":"ja0539443b00038\/ja0539443b00038_1","unstructured":"Compound10(ee= 85%):\u2009 [\u03b1]D,26\u00b0C= +29 (c= 0.84, CH2Cl2); CD (CH2Cl2, 9.7 \u00d7 10-3M, 20 \u00b0C):\u2009 \u03bb (\u0394\u03b5) 266 (+ 0.12), 303 (\u22120.20). Compound11(ee= 95%):\u2009 [\u03b1]D,25\u00b0C= \u2212142 (c= 0.84, CH2Cl2); CD (CH2Cl2, 1.7 \u00d7 10-3M, 20 \u00b0C):\u2009 \u03bb (\u0394\u03b5) 238 (+ 4.05), 310 (\u22123.33). Compound12(ee= 93%):\u2009 [\u03b1]D,25\u00b0C= \u221281 (c= 0.87, CH2Cl2); CD (CH2Cl2, 1.5 \u00d7 10-3M, 20 \u00b0C):\u2009 \u03bb (\u0394\u03b5) 246 (+ 1.73), 306 (\u22122.00)."},{"key":"ja0539443b00039\/ja0539443b00039_1","first-page":"912","volume":"905","author":"Brunner H.","year":"2001","journal-title":"Eur. J. Inorg. Chem."},{"key":"ja0539443b00040\/ja0539443b00040_1","first-page":"4441","volume":"4432","author":"Davenport A. J.","year":"2000","journal-title":"J. Chem. Soc., Dalton Trans."},{"key":"ja0539443b00041\/ja0539443b00041_1","first-page":"10413","volume":"115","author":"Ishihara K.","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"ja0539443b00042\/ja0539443b00042_1","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1107\/S0108767394006720","volume":"51","author":"Blessing R. H.","year":"1995","journal-title":"Acta Crystallogr."},{"key":"ja0539443b00043\/ja0539443b00043_1","volume-title":"Germany","author":"Package 0","year":"2000"},{"key":"ja0539443b00044\/ja0539443b00044_1","doi-asserted-by":"crossref","first-page":"881","DOI":"10.1107\/S0108767383001762","volume":"39","author":"Flack H. D.","year":"1983","journal-title":"Acta Crystallogr."}],"container-title":["Journal of the American Chemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ja0539443","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,1,30]],"date-time":"2024-01-30T04:34:37Z","timestamp":1706589277000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ja0539443"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2005,8,31]]},"references-count":59,"journal-issue":{"issue":"38","published-print":{"date-parts":[[2005,9,28]]}},"alternative-id":["10.1021\/ja0539443"],"URL":"https:\/\/doi.org\/10.1021\/ja0539443","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2005,8,31]]}}}