{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,26]],"date-time":"2026-09-26T17:40:28Z","timestamp":1790444428338,"version":"4.1.0"},"reference-count":81,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2014,11,20]],"date-time":"2014-11-20T00:00:00Z","timestamp":1416441600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2015,1,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Although phase\u2010transfer\u2010catalyzed asymmetric S<jats:sub>N<\/jats:sub>Ar reactions provide unique contribution to the catalytic asymmetric \u03b1\u2010arylations of carbonyl compounds to produce biologically active \u03b1\u2010aryl carbonyl compounds, the electrophiles were limited to arenes bearing strong electron\u2010withdrawing groups, such as a nitro group. To overcome this limitation, we examined the asymmetric S<jats:sub>N<\/jats:sub>Ar reactions of \u03b1\u2010amino acid derivatives with arene chromium complexes derived from fluoroarenes, including those containing electron\u2010donating substituents. The arylation was efficiently promoted by binaphthyl\u2010modified chiral phase\u2010transfer catalysts to give the corresponding \u03b1,\u03b1\u2010disubstituted \u03b1\u2010amino acids containing various aromatic substituents with high enantioselectivities.<\/jats:p>","DOI":"10.1002\/anie.201409065","type":"journal-article","created":{"date-parts":[[2014,11,20]],"date-time":"2014-11-20T23:09:03Z","timestamp":1416524943000},"page":"838-840","source":"Crossref","is-referenced-by-count":80,"title":["Phase\u2010Transfer\u2010Catalyzed Asymmetric S<sub>N<\/sub>Ar Reaction of \u03b1\u2010Amino Acid Derivatives with Arene Chromium Complexes"],"prefix":"10.1002","volume":"54","author":[{"given":"Seiji","family":"Shirakawa","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kenichiro","family":"Yamamoto","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Keiji","family":"Maruoka","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,11,20]]},"reference":[{"key":"e_1_2_2_1_2","unstructured":"For reviews on \u03b1\u2010arylation see:"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0028-1087673"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200903424"},{"key":"e_1_2_2_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200903424"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9000836"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0032-1316738"},{"key":"e_1_2_2_6_2","unstructured":"For examples of biologically active \u03b1\u2010aryl carbonyl compounds see:"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm001068s"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0004658"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1211\/0022357021778664"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm040077o"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm0496234"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2005.03.086"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2005.11.108"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0703231"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2007.02.060"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm100763j"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm300249m"},{"key":"e_1_2_2_18_2","unstructured":"For examples of catalytic asymmetric \u03b1\u2010arylations see:"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja973794z"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja017545t"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/b601691j"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja074453g"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja903880q"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja206047h"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja206050b"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2008906"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303602"},{"key":"e_1_2_2_27_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201303602"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527656141"},{"key":"e_1_2_2_29_2","unstructured":"For recent reviews on asymmetric phase\u2010transfer catalysis see:"},{"key":"e_1_2_2_30_2","first-page":"3","volume":"34","author":"O\u2019Donnell M. J.","year":"2001","journal-title":"Aldrichimica Acta"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020020e"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar0300625"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar030058t"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.2533\/000942906777674732"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200601737"},{"key":"e_1_2_2_35_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200601737"},{"key":"e_1_2_2_36_2","first-page":"77","volume":"40","author":"Ooi T.","year":"2007","journal-title":"Aldrichimica Acta"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr068368n"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/op7002979"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/b914028j"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201000019"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206835"},{"key":"e_1_2_2_41_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201206835"},{"key":"e_1_2_2_42_2","unstructured":"\u00a0"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja050200g"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo060627l"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201400004"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201403046"},{"key":"e_1_2_2_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201403046"},{"key":"e_1_2_2_47_2","unstructured":"For reviews on arene chromium complexes in organic synthesis see:"},{"key":"e_1_2_2_48_2","first-page":"938","author":"Kamikawa K.","year":"2000","journal-title":"Synlett"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0010-8545(01)00415-5"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1039\/b205479p"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0010-8545(03)00059-6"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/b606665h"},{"key":"e_1_2_2_53_2","unstructured":"\u00a0"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397918908054525"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-328X(90)87154-6"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)86468-1"},{"key":"e_1_2_2_57_2","unstructured":"For reviews on asymmetric syntheses of \u03b1 \u03b1\u2010disubstituted \u03b1\u2010amino acids see:"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(98)00391-7"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(99)00565-0"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500434"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1039\/B611091F"},{"key":"e_1_2_2_62_2","unstructured":"\u00a0"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0007051"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja021244h"},{"key":"e_1_2_2_65_2","unstructured":"\u00a0"},{"key":"e_1_2_2_66_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462257"},{"key":"e_1_2_2_66_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462257"},{"key":"e_1_2_2_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200800107"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.15227\/orgsyn.090.0121"},{"key":"e_1_2_2_69_2","unstructured":"\u00a0"},{"key":"e_1_2_2_70_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2005.09.185"},{"key":"e_1_2_2_71_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2007.02.079"},{"key":"e_1_2_2_72_2","unstructured":"For the preparation of saturated aqueous CsOH (80\u2005wt\u2009% aq. CsOH) see Ref.\u2005[12]."},{"key":"e_1_2_2_73_2","unstructured":"The reaction on larger scale (10 times) gave a similar result (74\u2009% yield 97\u2009%ee)."},{"key":"e_1_2_2_74_2","unstructured":"For details of the determination of the absolute configuration of3\u2009a see the Supporting Information."},{"key":"e_1_2_2_75_2","unstructured":"Racemic arene chromium complexes2\u2009c 2\u2009d and2\u2009fwere used for the reaction."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201409065","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201409065","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T09:25:54Z","timestamp":1697448354000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201409065"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,11,20]]},"references-count":81,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2015,1,12]]}},"alternative-id":["10.1002\/anie.201409065"],"URL":"https:\/\/doi.org\/10.1002\/anie.201409065","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,11,20]]}}}