{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,22]],"date-time":"2026-08-22T10:26:44Z","timestamp":1787394404188,"version":"build-2736575974"},"reference-count":101,"publisher":"Wiley","issue":"39","license":[{"start":{"date-parts":[[2023,8,3]],"date-time":"2023-08-03T00:00:00Z","timestamp":1691020800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2023,8,3]],"date-time":"2023-08-03T00:00:00Z","timestamp":1691020800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21871117, 91956203, 22071147, and 92256303"],"award-info":[{"award-number":["21871117, 91956203, 22071147, and 92256303"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100021187","name":"Beijing National Laboratory for Molecular Sciences","doi-asserted-by":"publisher","award":["BNLMS202109"],"award-info":[{"award-number":["BNLMS202109"]}],"id":[{"id":"10.13039\/501100021187","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":[[2023,9,25]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    An asymmetric intramolecular hydroalkylation of unactivated internal olefins with tethered cyclic ketones was realized by the cooperative catalysis of a newly designed chiral amine (SPD\u2010NH\n                    <jats:sub>2<\/jats:sub>\n                    ) and Pd\n                    <jats:sup>II<\/jats:sup>\n                    complex, providing straightforward access to either bridged or fused bicyclic systems containing three stereogenic centers with excellent enantioselectivity (up to 99\u2009% ee) and diastereoselectivity (up to &gt;20\u2009:\u20091 dr). Notably, the bicyclic products could be conveniently transformed into a diverse range of key structures frequently found in bioactive terpenes, such as \u0394\n                    <jats:sup>6<\/jats:sup>\n                    \u2010protoilludene, cracroson D, and vulgarisins. The steric hindrance between the Ar group of the SPD\u2010NH\n                    <jats:sub>2<\/jats:sub>\n                    catalyst and the branched chain of the substrate, hydrogen\u2010bonding interactions between the N\u2212H of the enamine motif and the C=O of the directing group MQ, and the counterion of the Pd\n                    <jats:sup>II<\/jats:sup>\n                    complex were identified as key factors for excellent stereoinduction in this dual catalytic process by density functional theory calculations.\n                  <\/jats:p>","DOI":"10.1002\/anie.202308858","type":"journal-article","created":{"date-parts":[[2023,7,18]],"date-time":"2023-07-18T07:04:44Z","timestamp":1689663884000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Asymmetric Intramolecular Hydroalkylation of Internal Olefin with Cycloalkanone to Directly Access Polycyclic Systems"],"prefix":"10.1002","volume":"62","author":[{"given":"Ai\u2010Fang","family":"Wang","sequence":"first","affiliation":[{"name":"School of Chemistry and Chemical Engineering Frontiers Science Center for Transformative Molecules Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University  Shanghai 200240 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jin\u2010Miao","family":"Tian","sequence":"additional","affiliation":[{"name":"College of Pharmaceutical Sciences &amp; Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals Zhejiang University of Technology  Hangzhou 310014 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiao\u2010Jing","family":"Zhao","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Frontiers Science Center for Transformative Molecules Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University  Shanghai 200240 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zi\u2010Hao","family":"Li","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Frontiers Science Center for Transformative Molecules Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University  Shanghai 200240 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ye","family":"Zhang","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Frontiers Science Center for Transformative Molecules Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University  Shanghai 200240 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ka","family":"Lu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering Lanzhou University  Lanzhou 730000 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hong","family":"Wang","sequence":"additional","affiliation":[{"name":"College of Pharmaceutical Sciences &amp; Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals Zhejiang University of Technology  Hangzhou 310014 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1811-4159","authenticated-orcid":false,"given":"Shu\u2010Yu","family":"Zhang","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Frontiers Science Center for Transformative Molecules Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University  Shanghai 200240 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9784-4052","authenticated-orcid":false,"given":"Yong\u2010Qiang","family":"Tu","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Frontiers Science Center for Transformative Molecules Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University  Shanghai 200240 P. R. China"},{"name":"State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering Lanzhou University  Lanzhou 730000 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tong\u2010Mei","family":"Ding","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Frontiers Science Center for Transformative Molecules Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University  Shanghai 200240 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu\u2010Yang","family":"Xie","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Frontiers Science Center for Transformative Molecules Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University  Shanghai 200240 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,8,3]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"For selected reviews on catalytic functionalization of alkenes see:"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300616"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr800420x"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100371y"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303916"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.5b00092"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201507151"},{"key":"e_1_2_7_8_1","unstructured":"\u00a0"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)86766-2"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr3001803"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c07489"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201004415"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b01471"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202206517"},{"key":"e_1_2_7_15_1","unstructured":"\u00a0"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7QO00613F"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.checat.2022.10.020"},{"key":"e_1_2_7_18_1","unstructured":"\u00a0"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.0c00164"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/cjoc.202100763"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c13482"},{"key":"e_1_2_7_22_1","unstructured":"\u00a0"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00463a069"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00535a026"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00370a076"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00385a053"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja011764x"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0293002"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol034879"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/om0498549"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja052836d"},{"key":"e_1_2_7_32_1","unstructured":"\u00a0"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1039\/c4qo00112e"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b02718"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b08383"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC03409F"},{"key":"e_1_2_7_37_1","unstructured":"\u00a0"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b00641"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b01350"},{"key":"e_1_2_7_40_1","unstructured":"\u00a0"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.8b04654"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201814272"},{"key":"e_1_2_7_43_1","unstructured":"\u00a0"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC02765A"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201501025"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b05386"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202114129"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201903435"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c01558"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202015001"},{"key":"e_1_2_7_51_1","unstructured":"\u00a0"},{"key":"e_1_2_7_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/b901258n"},{"key":"e_1_2_7_53_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2CS35258C"},{"key":"e_1_2_7_54_2","first-page":"505","volume":"30","author":"Han Z.","year":"2018","journal-title":"Prog. Chem."},{"key":"e_1_2_7_55_2","first-page":"1729","volume":"32","author":"Yu J.","year":"2020","journal-title":"Prog. Chem."},{"key":"e_1_2_7_56_1","unstructured":"\u00a0"},{"key":"e_1_2_7_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201008147"},{"key":"e_1_2_7_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201203406"},{"key":"e_1_2_7_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201306369"},{"key":"e_1_2_7_60_2","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms8332"},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201600529"},{"key":"e_1_2_7_62_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC00102C"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202001100"},{"key":"e_1_2_7_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202009238"},{"key":"e_1_2_7_65_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-29947-5"},{"key":"e_1_2_7_66_1","unstructured":"\u00a0"},{"key":"e_1_2_7_67_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2016.02.009"},{"key":"e_1_2_7_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b03330"},{"key":"e_1_2_7_69_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-11382-8"},{"key":"e_1_2_7_70_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-10398-4"},{"key":"e_1_2_7_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b01971"},{"key":"e_1_2_7_72_1","doi-asserted-by":"publisher","DOI":"10.1039\/b821070e"},{"key":"e_1_2_7_73_1","unstructured":"\u00a0"},{"key":"e_1_2_7_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201300349"},{"key":"e_1_2_7_75_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201500308"},{"key":"e_1_2_7_76_2","doi-asserted-by":"publisher","DOI":"10.1111\/1751-7915.13304"},{"key":"e_1_2_7_77_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2017.10.008"},{"key":"e_1_2_7_78_1","unstructured":"Deposition numbers2240125 (Cat\u20056) 2240126 (2\u2009f) 2242648 (2\u2009y) 2240119 (4\u2009e) 2240122 (4\u2009g) and 2250569 (5)contain 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_7_79_1","unstructured":"\u00a0"},{"key":"e_1_2_7_80_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejpb.2017.03.024"},{"key":"e_1_2_7_81_2","doi-asserted-by":"publisher","DOI":"10.3389\/fnmol.2018.00456"},{"key":"e_1_2_7_82_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202116136"},{"key":"e_1_2_7_83_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2022.113526"},{"key":"e_1_2_7_84_1","unstructured":"\u00a0"},{"key":"e_1_2_7_85_2","doi-asserted-by":"publisher","DOI":"10.1016\/0031-9422(91)84216-F"},{"key":"e_1_2_7_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b01278"},{"key":"e_1_2_7_87_1","doi-asserted-by":"publisher","DOI":"10.1504\/IJCBDD.2019.103600"},{"key":"e_1_2_7_88_1","unstructured":"\u00a0"},{"key":"e_1_2_7_89_2","doi-asserted-by":"publisher","DOI":"10.1039\/P19910001749"},{"key":"e_1_2_7_90_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1998-1982"},{"key":"e_1_2_7_91_1","unstructured":"\u00a0"},{"key":"e_1_2_7_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol901089h"},{"key":"e_1_2_7_93_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA08805H"},{"key":"e_1_2_7_94_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2021.132286"},{"key":"e_1_2_7_95_1","unstructured":"\u00a0"},{"key":"e_1_2_7_96_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja030032x"},{"key":"e_1_2_7_97_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo4026594"},{"key":"e_1_2_7_98_1","unstructured":"\u00a0"},{"key":"e_1_2_7_99_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0252-9602(18)30831-2"},{"key":"e_1_2_7_100_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jcp.2018.04.017"},{"key":"e_1_2_7_101_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10701-019-00257-z"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202308858","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202308858","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202308858","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,22]],"date-time":"2026-08-22T10:01:57Z","timestamp":1787392917000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202308858"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,8,3]]},"references-count":101,"journal-issue":{"issue":"39","published-print":{"date-parts":[[2023,9,25]]}},"alternative-id":["10.1002\/anie.202308858"],"URL":"https:\/\/doi.org\/10.1002\/anie.202308858","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,8,3]]},"assertion":[{"value":"2023-06-24","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-08-03","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202308858"}}