{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,2]],"date-time":"2026-07-02T18:09:48Z","timestamp":1783015788386,"version":"3.54.6"},"reference-count":69,"publisher":"Wiley","issue":"49","license":[{"start":{"date-parts":[[2013,10,9]],"date-time":"2013-10-09T00:00:00Z","timestamp":1381276800000},"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":[[2013,12,2]]},"DOI":"10.1002\/anie.201306443","type":"journal-article","created":{"date-parts":[[2013,10,12]],"date-time":"2013-10-12T02:45:14Z","timestamp":1381545914000},"page":"12956-12960","source":"Crossref","is-referenced-by-count":14,"title":["Enantiodivergent Deprotonation\/Acylation of \u03b1\u2010Amino Nitriles"],"prefix":"10.1002","volume":"52","author":[{"given":"Michiko","family":"Sasaki","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tomo","family":"Takegawa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kunihiro","family":"Sakamoto","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuri","family":"Kotomori","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuko","family":"Otani","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tomohiko","family":"Ohwada","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masatoshi","family":"Kawahata","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kentaro","family":"Yamaguchi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kei","family":"Takeda","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,10,9]]},"reference":[{"key":"e_1_2_3_1_2","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","first-page":"1","volume":"31","author":"Arseniyadis S.","year":"1984","journal-title":"Org. React."},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)01134-6"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo802241x"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc00082b"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/chir.10222"},{"key":"e_1_2_3_7_2","unstructured":"For enantioselective trapping of a cyclopropylnitirile carbanion see:"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00871a050"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00711a040"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.11.012"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol070149g"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201102253"},{"key":"e_1_2_3_13_2","unstructured":"also see ref.\u2005[3]."},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19840961205"},{"key":"e_1_2_3_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198409321"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201303442"},{"key":"e_1_2_3_15_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303442"},{"key":"e_1_2_3_16_2","unstructured":"\u00a0"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00022a065"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00034a007"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)90460-0"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00273a042"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19820650141"},{"key":"e_1_2_3_22_2","unstructured":"\u00a0"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1007\/3-540-36117-0_5"},{"key":"e_1_2_3_24_2","first-page":"186","volume-title":"Organolithiums: Selectivity for Synthesis","author":"Clayden J.","year":"2002"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2012.10.016"},{"key":"e_1_2_3_26_2","volume-title":"Stereochemical Aspects of Organolithium Compounds, Topics in Stereochemistry, Vol.\u200526","author":"Kizirian J.\u2010C.","year":"2010"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19870700704"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)02156-5"},{"key":"e_1_2_3_29_2","unstructured":"\u00a0"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00025a057"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19810931112"},{"key":"e_1_2_3_31_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198109711"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0365781"},{"key":"e_1_2_3_33_2","unstructured":"\u00a0"},{"key":"e_1_2_3_34_2","first-page":"282","volume-title":"Dynamic Stereochemistry of Chiral Compounds: Principles and Applications","author":"Wolf C.","year":"2008"},{"key":"e_1_2_3_35_2","volume-title":"Stereochemical Aspects of Organolithium Compounds, Topics in Stereochemistry, Vol.\u200526","author":"Carlier P. R.","year":"2010"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19961082304"},{"key":"e_1_2_3_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199627081"},{"key":"e_1_2_3_37_2","unstructured":"For a review of ketene imines see:"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs35159e"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201202139"},{"key":"e_1_2_3_39_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201202139"},{"key":"e_1_2_3_40_2","unstructured":"For diastereoselective substitution of lithiated \u03b1\u2010amino nitriles containing a remote chiral auxiliary see:"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0705519"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-0690(199801)1998:1<63::AID-EJOC63>3.0.CO;2-H"},{"key":"e_1_2_3_43_2","unstructured":"\u00a0"},{"key":"e_1_2_3_44_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.05.110"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19891010306"},{"key":"e_1_2_3_45_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198902771"},{"key":"e_1_2_3_46_2","unstructured":"Garc\u00eda\u2005Ruano and Mart\u00edn\u2010Castro have reported that carbanions derived from \u03b1\u2010alkyl phenylacetonitriles bearing a sulfinyl group as a remote chiral auxiliary show a stereodivergent behavior in their reactions with carbon electrophiles in the presence of KHMDS or NaHMDS. The stereodivergence is rationalized by a planar or pyramidal structure for the preformed benzylic carbanions:"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo2004204"},{"key":"e_1_2_3_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200903521"},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0670761"},{"key":"e_1_2_3_50_2","unstructured":"\u00a0"},{"key":"e_1_2_3_51_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)90461-2"},{"key":"e_1_2_3_52_2","doi-asserted-by":"publisher","DOI":"10.1007\/3-540-36117-0_4"},{"key":"e_1_2_3_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201100970"},{"key":"e_1_2_3_54_2","unstructured":"For deprotonative lithiation assisted by the formation of a prelithiation complex see:"},{"key":"e_1_2_3_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200300590"},{"key":"e_1_2_3_55_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300590"},{"key":"e_1_2_3_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar950142b"},{"key":"e_1_2_3_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200603038"},{"key":"e_1_2_3_57_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200603038"},{"key":"e_1_2_3_58_2","unstructured":"The reported pKavalues for diisopropylamine and hexamethyldisilazane in THF are 34.4 and 23.1 respectively:"},{"key":"e_1_2_3_59_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)82054-8"},{"key":"e_1_2_3_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo202253q"},{"key":"e_1_2_3_61_2","unstructured":"We assume that (S)\u20104immediately racemizes after deprotonation unless an electrophile exists. This assumption is based on the fact that deprotonation by LDA or NaHMDS over a 2\u2005min period at \u2212100\u2009\u00b0C followed by proton quenching by precooled AcOH in THF led to recovery of completely racemized starting material."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201306443","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201306443","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T09:24:41Z","timestamp":1697448281000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201306443"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,10,9]]},"references-count":69,"journal-issue":{"issue":"49","published-print":{"date-parts":[[2013,12,2]]}},"alternative-id":["10.1002\/anie.201306443"],"URL":"https:\/\/doi.org\/10.1002\/anie.201306443","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,10,9]]}}}