{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,10]],"date-time":"2026-10-10T07:59:11Z","timestamp":1791619151339,"version":"4.3.4"},"reference-count":62,"publisher":"Wiley","issue":"45","license":[{"start":{"date-parts":[[2023,9,28]],"date-time":"2023-09-28T00:00:00Z","timestamp":1695859200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001381","name":"National Research Foundation Singapore","doi-asserted-by":"publisher","award":["A-0004067-00-02"],"award-info":[{"award-number":["A-0004067-00-02"]}],"id":[{"id":"10.13039\/501100001381","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":[[2023,11,6]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Chiral \u03b1,\u03b1\u2010diaryl ketones are structural motifs commonly present in bioactive molecules, and they are also valuable building blocks in synthetic organic chemistry. However, catalytic asymmetric synthesis of \u03b1,\u03b1\u2010diaryl ketones bearing a tertiary stereogenic center remains largely unsolved. Herein, we report a catalytic de novo enantioselective synthesis of \u03b1,\u03b1\u2010diaryl ketones from simple alkynes via chiral phosphoric acid (CPA) catalysis. A broad range of enolizable \u03b1,\u03b1\u2010diaryl ketones are prepared in good yields and with excellent enantioselectivities. The described protocol also serves as an efficient deuteration method for the preparation of enantiomerically enriched deuterated \u03b1,\u03b1\u2010diaryl ketones. Using the methodology reported, bioactive molecules, including one of the best\u2010selling anti\u2010breast cancer drugs, tamoxifen, are readily synthesized.<\/jats:p>","DOI":"10.1002\/anie.202310078","type":"journal-article","created":{"date-parts":[[2023,9,19]],"date-time":"2023-09-19T04:32:45Z","timestamp":1695097965000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":25,"title":["Enantioselective\n                    <i>De Novo<\/i>\n                    Synthesis of \u03b1,\u03b1\u2010Diaryl Ketones from Alkynes"],"prefix":"10.1002","volume":"62","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6847-5366","authenticated-orcid":false,"given":"Xueting","family":"Zhou","sequence":"first","affiliation":[{"name":"Joint School of National University of Singapore Tianjin University  International Campus of Tianjin University Binhai New City Fuzhou 350207 China"},{"name":"Department of Chemistry National University of Singapore  3 Science Drive 3 117543 Singapore Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qingqin","family":"Huang","sequence":"additional","affiliation":[{"name":"Joint School of National University of Singapore Tianjin University  International Campus of Tianjin University Binhai New City Fuzhou 350207 China"},{"name":"Department of Chemistry National University of Singapore  3 Science Drive 3 117543 Singapore Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiami","family":"Guo","sequence":"additional","affiliation":[{"name":"Joint School of National University of Singapore Tianjin University  International Campus of Tianjin University Binhai New City Fuzhou 350207 China"},{"name":"Department of Chemistry National University of Singapore  3 Science Drive 3 117543 Singapore Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4225-7408","authenticated-orcid":false,"given":"Lei","family":"Dai","sequence":"additional","affiliation":[{"name":"Department of Chemistry National University of Singapore  3 Science Drive 3 117543 Singapore Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5730-166X","authenticated-orcid":false,"given":"Yixin","family":"Lu","sequence":"additional","affiliation":[{"name":"Joint School of National University of Singapore Tianjin University  International Campus of Tianjin University Binhai New City Fuzhou 350207 China"},{"name":"Department of Chemistry National University of Singapore  3 Science Drive 3 117543 Singapore Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,9,28]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197204601"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja103183r"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b05086"},{"key":"e_1_2_3_5_2","unstructured":"M. Allegretti R. Bertini M.\u2005C. Cesta C. Bizzarri F. Colotta WO2004052830\u2005A1 2004."},{"key":"e_1_2_3_6_1","unstructured":"\u00a0"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar0201106"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200903424"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b04480"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja074453g"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja501815p"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b09580"},{"key":"e_1_2_3_13_1","unstructured":"\u00a0"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200804888"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja909689t"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja402922w"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201300621"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c13236"},{"key":"e_1_2_3_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202008528"},{"key":"e_1_2_3_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c01489"},{"key":"e_1_2_3_21_1","doi-asserted-by":"publisher","DOI":"10.31635\/ccschem.021.202000720"},{"key":"e_1_2_3_22_1","unstructured":"\u00a0"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1080\/14786419.2018.1443091"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2008.06.001"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00197a018"},{"key":"e_1_2_3_26_1","unstructured":"\u00a0"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0201068"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500691k"},{"key":"e_1_2_3_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201804955"},{"key":"e_1_2_3_30_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1cs15268h"},{"key":"e_1_2_3_31_1","unstructured":"\u00a0"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300503r"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201709766"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c01416"},{"key":"e_1_2_3_35_1","unstructured":"\u00a0"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/c9pp00148d"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c09248"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-020-0541-1"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c02316"},{"key":"e_1_2_3_40_1","unstructured":"\u00a0"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201800415"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1038\/s44160-022-00072-x"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9727530"},{"key":"e_1_2_3_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol000110a"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b13113"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.add2574"},{"key":"e_1_2_3_47_1","unstructured":"Deposition number2252104 (for5\u2009n)contains 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_48_1","unstructured":"\u00a0"},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00250a027"},{"key":"e_1_2_3_50_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jcat.2006.12.016"},{"key":"e_1_2_3_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201107334"},{"key":"e_1_2_3_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/C0CS00113A"},{"key":"e_1_2_3_53_1","unstructured":"\u00a0"},{"key":"e_1_2_3_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlcr.1825"},{"key":"e_1_2_3_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201704146"},{"key":"e_1_2_3_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.8b01808"},{"key":"e_1_2_3_57_1","unstructured":"\u00a0"},{"key":"e_1_2_3_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00795"},{"key":"e_1_2_3_59_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS01496F"},{"key":"e_1_2_3_60_1","unstructured":"\u00a0"},{"key":"e_1_2_3_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206024"},{"key":"e_1_2_3_62_2","doi-asserted-by":"publisher","DOI":"10.2165\/00003495-197816010-00001"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202310078","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,28]],"date-time":"2023-10-28T01:11:41Z","timestamp":1698455501000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202310078"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,9,28]]},"references-count":62,"journal-issue":{"issue":"45","published-print":{"date-parts":[[2023,11,6]]}},"alternative-id":["10.1002\/anie.202310078"],"URL":"https:\/\/doi.org\/10.1002\/anie.202310078","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,9,28]]},"assertion":[{"value":"2023-07-15","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-09-28","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202310078"}}