{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T15:53:23Z","timestamp":1790006003749,"version":"4.0.1"},"reference-count":67,"publisher":"Wiley","issue":"21","license":[{"start":{"date-parts":[[2018,4,23]],"date-time":"2018-04-23T00:00:00Z","timestamp":1524441600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000009","name":"Foundation for the National Institutes of Health","doi-asserted-by":"publisher","award":["GM-068649"],"award-info":[{"award-number":["GM-068649"]}],"id":[{"id":"10.13039\/100000009","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":[[2018,5,22]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Catalyst control over reactions that produce multiple stereoisomers is a challenge in synthesis. Control over reactions that involve stereogenic elements remote from one another is particularly uncommon. Additionally, catalytic reactions that address both stereogenic carbon centers and an element of axial chirality are also rare. Reported herein is a catalytic approach to each stereoisomer of a scaffold containing a stereogenic center remote from an axis of chirality. Newly developed peptidyl copper complexes catalyze an unprecedented remote desymmetrization involving enantioselective C\u2212N bond\u2010forming cross\u2010coupling. Then, chiral phosphoric acid catalysts set an axis of chirality through an unprecedented atroposelective cyclodehydration to form a heterocycle with high diastereoselectivity. The application of chiral copper complexes and phosphoric acids provides access to each stereoisomer of a framework with two different elements of stereogenicity.<\/jats:p>","DOI":"10.1002\/anie.201802963","type":"journal-article","created":{"date-parts":[[2018,4,11]],"date-time":"2018-04-11T01:36:25Z","timestamp":1523410585000},"page":"6251-6255","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":131,"title":["Divergent Control of Point and Axial Stereogenicity: Catalytic Enantioselective C\u2212N Bond\u2010Forming Cross\u2010Coupling and Catalyst\u2010Controlled Atroposelective Cyclodehydration"],"prefix":"10.1002","volume":"57","author":[{"given":"Yongseok","family":"Kwon","sequence":"first","affiliation":[{"name":"Department of Chemistry Yale University  225 Prospect Street New Haven CT 06520-8107 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alex J.","family":"Chinn","sequence":"additional","affiliation":[{"name":"Department of Chemistry Yale University  225 Prospect Street New Haven CT 06520-8107 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Byoungmoo","family":"Kim","sequence":"additional","affiliation":[{"name":"Department of Chemistry Yale University  225 Prospect Street New Haven CT 06520-8107 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7817-1318","authenticated-orcid":false,"given":"Scott J.","family":"Miller","sequence":"additional","affiliation":[{"name":"Department of Chemistry Yale University  225 Prospect Street New Haven CT 06520-8107 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,4,23]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.3109\/9781420092394"},{"key":"e_1_2_2_2_1","unstructured":"\u00a0"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-58571-5"},{"key":"e_1_2_2_4_2","volume-title":"Comprehensive Chirality","author":"Yamamoto H.","year":"2012"},{"key":"e_1_2_2_5_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b13340"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201601188"},{"key":"e_1_2_2_8_1","unstructured":"\u00a0"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature17191"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201106321"},{"key":"e_1_2_2_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201106321"},{"key":"e_1_2_2_11_1","unstructured":"\u00a0"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja055545d"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja060312n"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1024"},{"key":"e_1_2_2_15_1","unstructured":"\u00a0"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1237068"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201504749"},{"key":"e_1_2_2_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201504749"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b11692"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b10680"},{"key":"e_1_2_2_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CY01319A"},{"key":"e_1_2_2_21_1","unstructured":"\u00a0"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200901719"},{"key":"e_1_2_2_22_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200901719"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm200584g"},{"key":"e_1_2_2_24_1","unstructured":"\u00a0"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.190103402141"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1237175"},{"key":"e_1_2_2_27_1","unstructured":"\u00a0"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b03444"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b11197"},{"key":"e_1_2_2_30_1","unstructured":"For selected examples see:"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b02783"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja408864c"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b03091"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303816"},{"key":"e_1_2_2_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201303816"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200801030"},{"key":"e_1_2_2_35_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200801030"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja909571z"},{"key":"e_1_2_2_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3md00088e"},{"key":"e_1_2_2_38_1","unstructured":"\u00a0"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aad8313"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2016.04.049"},{"key":"e_1_2_2_41_1","unstructured":"For recent examples of atroposelective cyclizations see:"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b04337"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.7b00602"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201709182"},{"key":"e_1_2_2_44_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201709182"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201510259"},{"key":"e_1_2_2_45_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201510259"},{"key":"e_1_2_2_46_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201600041"},{"key":"e_1_2_2_47_1","unstructured":"\u00a0"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200353240"},{"key":"e_1_2_2_48_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200353240"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0491533"},{"key":"e_1_2_2_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201505898"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201505898"},{"key":"e_1_2_2_51_1","unstructured":"See the Supporting Information for details."},{"key":"e_1_2_2_52_1","doi-asserted-by":"publisher","DOI":"10.2165\/00003495-200464050-00008"},{"key":"e_1_2_2_53_1","volume-title":"Asymmetric Bronsted Acid Catalysis","author":"Rueping M.","year":"2016"},{"key":"e_1_2_2_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja057444l"},{"key":"e_1_2_2_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja963666v"},{"key":"e_1_2_2_56_1","unstructured":"See the Supporting Information for structure and details. CCDC\u20051589152 and 1589151((R aS)-4\u2009jand (S aR)-4\u2009j) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge fromThe Cambridge Crystallographic Data Centre."},{"key":"e_1_2_2_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm200504p"},{"key":"e_1_2_2_58_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2017.11.050"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201802963","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201802963","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.201802963","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201802963","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,30]],"date-time":"2023-08-30T19:52:19Z","timestamp":1693425139000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201802963"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,4,23]]},"references-count":67,"journal-issue":{"issue":"21","published-print":{"date-parts":[[2018,5,22]]}},"alternative-id":["10.1002\/anie.201802963"],"URL":"https:\/\/doi.org\/10.1002\/anie.201802963","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,4,23]]},"assertion":[{"value":"2018-03-10","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-04-23","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}