{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,5,13]],"date-time":"2025-05-13T22:08:24Z","timestamp":1747174104580,"version":"3.40.5"},"reference-count":34,"publisher":"American Chemical Society (ACS)","issue":"7","license":[{"start":{"date-parts":[[2023,3,20]],"date-time":"2023-03-20T00:00:00Z","timestamp":1679270400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2023,3,20]],"date-time":"2023-03-20T00:00:00Z","timestamp":1679270400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2023,3,20]],"date-time":"2023-03-20T00:00:00Z","timestamp":1679270400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2023,4,7]]},"DOI":"10.1021\/acs.joc.2c02993","type":"journal-article","created":{"date-parts":[[2023,3,20]],"date-time":"2023-03-20T16:47:30Z","timestamp":1679330850000},"page":"4387-4396","source":"Crossref","is-referenced-by-count":1,"title":["Small Change, Big Impact: Reversal of Diastereoselection in Cuprate Conjugate Additions to \u03b1,\u03b2-Unsaturated Lactams and Identification of a Competing Mechanism"],"prefix":"10.1021","volume":"88","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9785-5077","authenticated-orcid":true,"given":"Stephen W.","family":"Wright","sequence":"first","affiliation":[{"name":"Medicine Design, Pfizer Global Research and Development, 445 Eastern Point Road, Groton, Connecticut 06340, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3459-3767","authenticated-orcid":true,"given":"Chulho","family":"Choi","sequence":"additional","affiliation":[{"name":"Medicine Design, Pfizer Global Research and Development, 445 Eastern Point Road, Groton, Connecticut 06340, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5515-9612","authenticated-orcid":true,"given":"Yu","family":"Kawamata","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9193-9053","authenticated-orcid":true,"given":"Phil S.","family":"Baran","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"316","published-online":{"date-parts":[[2023,3,20]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b02533"},{"key":"ref2\/cit2a","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.06.111"},{"key":"ref2\/cit2b","doi-asserted-by":"publisher","DOI":"10.1021\/ja0522783"},{"key":"ref3\/cit3","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.7b00231"},{"key":"ref4\/cit4","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.8b00386"},{"key":"ref5\/cit5a","unstructured":"(a)Jorand-Lebrun, C.; Boivin, R. Preparation of Quinoline Compounds as IRAK Inhibitors and Uses Thereof. WO 149 522 A1, 2019."},{"key":"ref5\/cit5b","unstructured":"(b)Mainolfi, N.; Ji, N.; Kluge, A. F.; Weiss, M. M.; Zhang, Y. Preparation of Peptide Conjugates as IRAK4 Protein Kinase Degraders. US 192 668 A1, 2019."},{"key":"ref5\/cit5c","unstructured":"(c)Xie, Y.; Babiss, L. E. Preparation of Heterocyclic Compounds as IRAK4 Inhibitors. WO 089 422 A1, 2019."},{"key":"ref6\/cit6","doi-asserted-by":"publisher","DOI":"10.1021\/jo100628v"},{"key":"ref7\/cit7","doi-asserted-by":"publisher","DOI":"10.1039\/D1CS00564B"},{"key":"ref8\/cit8","doi-asserted-by":"publisher","DOI":"10.1139\/v08-059"},{"key":"ref9\/cit9","doi-asserted-by":"publisher","DOI":"10.1021\/jo300347k"},{"key":"ref10\/cit10","doi-asserted-by":"publisher","DOI":"10.1021\/ja01084a034"},{"key":"ref11\/cit11","doi-asserted-by":"publisher","DOI":"10.1021\/jo9816109"},{"key":"ref12\/cit12","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)10746-8"},{"key":"ref13\/cit13","doi-asserted-by":"publisher","DOI":"10.1021\/ja00712a032"},{"key":"ref14\/cit14","doi-asserted-by":"publisher","DOI":"10.1021\/ar50098a003"},{"key":"ref15\/cit15","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)95114-1"},{"key":"ref16\/cit16","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)95113-X"},{"key":"ref17\/cit17","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)84901-1"},{"key":"ref18\/cit18","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)90543-5"},{"key":"ref19\/cit19","doi-asserted-by":"publisher","DOI":"10.1021\/ja00073a052"},{"key":"ref20\/cit20","doi-asserted-by":"publisher","DOI":"10.1021\/ja00149a032"},{"key":"ref21\/cit21","doi-asserted-by":"publisher","DOI":"10.1021\/jo040216+"},{"key":"ref22\/cit22","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)02388-7"},{"key":"ref23\/cit23","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)98309-6"},{"key":"ref24\/cit24","doi-asserted-by":"publisher","DOI":"10.1016\/0022-328X(89)87041-X"},{"key":"ref25\/cit25","doi-asserted-by":"publisher","DOI":"10.1021\/jo00077a055"},{"key":"ref26\/cit26","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19980817)37:15<2099::AID-ANIE2099>3.0.CO;2-U"},{"key":"ref27\/cit27","unstructured":"Calculations\nwere performed using\nSpartan\u201920, Version 1.1.4, released Jan 21 2022 from Wavefunction.\nCalculations were done at the DFT EDF2 6-31+G* level of theory."},{"key":"ref28\/cit28a","doi-asserted-by":"publisher","DOI":"10.1021\/ja993349z"},{"key":"ref28\/cit28b","doi-asserted-by":"publisher","DOI":"10.1021\/ja0375176"},{"key":"ref29\/cit29","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2009.03.011"},{"key":"ref30\/cit30","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2012.09.093"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.2c02993","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.2c02993","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,7]],"date-time":"2023-04-07T09:31:36Z","timestamp":1680859896000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/acs.joc.2c02993"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,3,20]]},"references-count":34,"journal-issue":{"issue":"7","published-print":{"date-parts":[[2023,4,7]]}},"alternative-id":["10.1021\/acs.joc.2c02993"],"URL":"https:\/\/doi.org\/10.1021\/acs.joc.2c02993","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"type":"print","value":"0022-3263"},{"type":"electronic","value":"1520-6904"}],"subject":[],"published":{"date-parts":[[2023,3,20]]}}}