{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,14]],"date-time":"2026-09-14T10:02:58Z","timestamp":1789380178434,"version":"build-2803163510"},"reference-count":50,"publisher":"Wiley","issue":"38","license":[{"start":{"date-parts":[[2026,7,11]],"date-time":"2026-07-11T00:00:00Z","timestamp":1783728000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,7,11]],"date-time":"2026-07-11T00:00:00Z","timestamp":1783728000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001711","name":"Schweizerischer Nationalfonds zur F\u00f6rderung der Wissenschaftlichen Forschung","doi-asserted-by":"publisher","award":["200020_188729"],"award-info":[{"award-number":["200020_188729"]}],"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":[[2026,9,14]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>Cyclic imines are common intermediates in the biosynthesis of alkaloids, but their use in enantioselective organic synthesis is limited by their high reactivity and tendency to trimerize. Here, we present a mild organocatalytic method for the stereoselective addition of malonates to cyclic imines. Under carefully optimized conditions that suppress background reactivity, cinchona alkaloid\u2010derived catalysts enabled access to \u03b1\u2010functionalized pyrrolidines and 5\u20106\u20105 and 6\u20106\u20105 tricycles in high yields and stereoselectivity. Mechanistic studies revealed that the catalyst controls the stereochemistry of the initial addition, while subsequent reactions are governed by the substrate. The total synthesis of the alkaloid Tetraponerine T\u20101, the shortest route reported to date, highlights the synthetic utility of the methodology.<\/jats:p>","DOI":"10.1002\/anie.8336123","type":"journal-article","created":{"date-parts":[[2026,7,11]],"date-time":"2026-07-11T17:19:21Z","timestamp":1783790361000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Organocatalytic Enantioselective Addition of Malonates to Cyclic Imines: A Short Total Synthesis of Tetraponerine T\u20101"],"prefix":"10.1002","volume":"65","author":[{"given":"Frederic","family":"K\u00f6lblin","sequence":"first","affiliation":[{"name":"Laboratory of Organic Chemistry ETH Z\u00fcrich  Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3075-5741","authenticated-orcid":false,"given":"Helma","family":"Wennemers","sequence":"additional","affiliation":[{"name":"Laboratory of Organic Chemistry ETH Z\u00fcrich  Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,7,11]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/9780470742761"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm4017625"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm501100b"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c06584"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2871"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202313247"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol2017406"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0636791"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01840"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b03253"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c04558"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3CS60321K"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr980414z"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/b515725k"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201310532"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1515\/znc\u20101987\u20100520"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF01013903"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1023\/B:CEMN.0000023628.65936.a7"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200900064"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1139\/v94\u2010016"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/a608180k"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040\u20104020(94)01030\u20104"},{"key":"e_1_2_8_24_1","first-page":"24","article-title":"Concise Total Synthesis and Stereochemical Analysis of Tetraponerines T3 and T4","volume":"79","author":"For examples, see","year":"2014","journal-title":"Journal of Organic Chemistry"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00291a007"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo960398a"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo302045y"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201504845"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1055\/s\u20100034\u20101380215"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b00837"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja001688i"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo991034w"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201100282"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1139\/v00\u2010096"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200501721"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1039\/b508833j"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol050431s"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja044370p"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja805693p"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200702187"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201607146"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol017117s"},{"key":"e_1_2_8_43_1","unstructured":"Deposition numbers 2542707 (for3a) 2542708 (for3c) and 2542709 (forent\u20104a) contain the supplementary crystallographic data for this paper. 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