{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T06:40:02Z","timestamp":1788417602176,"version":"build-2803163510"},"reference-count":71,"publisher":"Wiley","issue":"19","license":[{"start":{"date-parts":[[2022,3,11]],"date-time":"2022-03-11T00:00:00Z","timestamp":1646956800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001711","name":"Schweizerischer Nationalfonds zur F\u00f6rderung der Wissenschaftlichen Forschung","doi-asserted-by":"publisher","award":["SNSF 200020-169077"],"award-info":[{"award-number":["SNSF 200020-169077"]}],"id":[{"id":"10.13039\/501100001711","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2022,5,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The asymmetric Pictet\u2013Spengler reaction (PSR) with aldehydes is well known. However, PSR involving ketones as electrophilic partners is far\u2010less developed. We report herein the first examples of catalytic enantioselective PSR of tryptamines with \u03b1\u2010ketoamides. A new class of easily accessible prolyl\u2010urea organocatalysts bearing a single H\u2010bond donor function catalyzes the title reaction to afford 1,1\u2010disubstituted tetrahydro\u2010\u03b2\u2010carbolines in excellent yields and enantioselectivities. The kinetic isotope effect using C2\u2010deuterium\u2010labelled tryptamine indicates that the rearomatization of the pentahydro\u2010\u03b2\u2010carbolinium ion intermediate might be the rate\u2010 and the enantioselectivity\u2010determining step.<\/jats:p>","DOI":"10.1002\/anie.202201788","type":"journal-article","created":{"date-parts":[[2022,2,28]],"date-time":"2022-02-28T13:03:41Z","timestamp":1646053421000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":41,"title":["Catalytic Enantioselective Pictet\u2013Spengler Reaction of \u03b1\u2010Ketoamides Catalyzed by a Single H\u2010Bond Donor Organocatalyst"],"prefix":"10.1002","volume":"61","author":[{"given":"R\u00e9mi","family":"Andres","sequence":"first","affiliation":[{"name":"Laboratory of Synthesis and Natural Products Institute of Chemical Sciences and Engineering Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne, EPFL-SB-ISIC-LSPN, BCH  5304, 1015 Lausanne Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qian","family":"Wang","sequence":"additional","affiliation":[{"name":"Laboratory of Synthesis and Natural Products Institute of Chemical Sciences and Engineering Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne, EPFL-SB-ISIC-LSPN, BCH  5304, 1015 Lausanne Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8390-6689","authenticated-orcid":false,"given":"Jieping","family":"Zhu","sequence":"additional","affiliation":[{"name":"Laboratory of Synthesis and Natural Products Institute of Chemical Sciences and Engineering Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne, EPFL-SB-ISIC-LSPN, BCH  5304, 1015 Lausanne Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,3,11]]},"reference":[{"key":"e_1_2_3_1_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2018.08.027"},{"key":"e_1_2_3_2_1","unstructured":"\u00a0"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19110440309"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201008071"},{"key":"e_1_2_3_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201008071"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0036-1589003"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2019.01.004"},{"key":"e_1_2_3_7_1","unstructured":"\u00a0"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja046259p"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol802887h"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol403773a"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b06811"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b07846"},{"key":"e_1_2_3_13_1","unstructured":"\u00a0"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja057444l"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701808"},{"key":"e_1_2_3_15_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200701808"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo8010478"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201103207"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0032-1318302"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201703178"},{"key":"e_1_2_3_19_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201703178"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202100363"},{"key":"e_1_2_3_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202100363"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202102518"},{"key":"e_1_2_3_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202102518"},{"key":"e_1_2_3_22_1","unstructured":"\u00a0"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB02606D"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c05804"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202109694"},{"key":"e_1_2_3_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202109694"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja805693p"},{"key":"e_1_2_3_27_1","unstructured":"\u00a0"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja076179w"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol800256j"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9024885"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol101651t"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol302215u"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol401784h"},{"key":"e_1_2_3_34_1","unstructured":"\u00a0"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2011.08.071"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201100050"},{"key":"e_1_2_3_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b03656"},{"key":"e_1_2_3_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja077190z"},{"key":"e_1_2_3_39_1","unstructured":"\u00a0"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200806110"},{"key":"e_1_2_3_40_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200806110"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol300922b"},{"key":"e_1_2_3_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC00882J"},{"key":"e_1_2_3_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c04316"},{"key":"e_1_2_3_44_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.89.23.11456"},{"key":"e_1_2_3_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol501856v"},{"key":"e_1_2_3_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b00478"},{"key":"e_1_2_3_47_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB02565G"},{"key":"e_1_2_3_48_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11030-005-1292-z"},{"key":"e_1_2_3_49_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc04447d"},{"key":"e_1_2_3_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr068377w"},{"key":"e_1_2_3_51_1","unstructured":"\u00a0"},{"key":"e_1_2_3_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200704840"},{"key":"e_1_2_3_52_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200704840"},{"key":"e_1_2_3_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo100302y"},{"key":"e_1_2_3_54_1","unstructured":"Deposition numbers\u20052144710 (S)-7\u2009qand 2146796 (+)-6\u2009econtain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."},{"key":"e_1_2_3_55_1","unstructured":"B. K.Handa P. J.Machin J. A.Martin S.Redshaw G. J.Thomas D\u00e9riv\u00e9s d'amminoacidesEP0346847\u2005A2 1989."},{"key":"e_1_2_3_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr200398y"},{"key":"e_1_2_3_57_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6MB00850J"},{"key":"e_1_2_3_58_1","unstructured":"\u00a0"},{"key":"e_1_2_3_59_2","doi-asserted-by":"publisher","DOI":"10.1039\/b107298f"},{"key":"e_1_2_3_60_2","doi-asserted-by":"publisher","DOI":"10.1039\/b511216h"},{"key":"e_1_2_3_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201205449"},{"key":"e_1_2_3_61_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201205449"},{"key":"e_1_2_3_62_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aao5894"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202201788","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202201788","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202201788","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,23]],"date-time":"2023-08-23T19:37:14Z","timestamp":1692819434000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202201788"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,3,11]]},"references-count":71,"journal-issue":{"issue":"19","published-print":{"date-parts":[[2022,5,2]]}},"alternative-id":["10.1002\/anie.202201788"],"URL":"https:\/\/doi.org\/10.1002\/anie.202201788","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,3,11]]},"assertion":[{"value":"2022-02-01","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-03-11","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202201788"}}