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Soc. Rev.<\/i>, 42<\/b>, 4918\u20134931 (2013).","DOI":"10.1039\/c3cs35496b"},{"key":"2","doi-asserted-by":"crossref","unstructured":"2) Zhu S.-F., Zhou Q.-L., Acc. Chem. Res.<\/i>, 45<\/b>, 1365\u20131377 (2012).","DOI":"10.1021\/ar300051u"},{"key":"3","doi-asserted-by":"crossref","unstructured":"3) Ren Y.-Y., Zhu S.-F., Zhou Q.-L., Org. Biomol. Chem.<\/i>, 16<\/b>, 3087\u20133094 (2018).","DOI":"10.1039\/C8OB00473K"},{"key":"4","doi-asserted-by":"crossref","unstructured":"4) Liu B., Zhu S.-F., Zhang W., Chen C., Zhou Q.-L., J. Am. Chem. Soc.<\/i>, 129<\/b>, 5834\u20135835 (2007).","DOI":"10.1021\/ja0711765"},{"key":"5","doi-asserted-by":"crossref","unstructured":"5) Zhu S.-F., Xu B., Wang G.-P., Zhou Q.-L., J. Am. Chem. Soc.<\/i>, 134<\/b>, 436\u2013442 (2012).","DOI":"10.1021\/ja2084493"},{"key":"6","doi-asserted-by":"crossref","unstructured":"6) Hou Z., Wang J., He P., Wang J., Qin B., Liu X., Lin L., Feng X., Angew. Chem. Int. Ed.<\/i>, 49<\/b>, 4763\u20134766 (2010).","DOI":"10.1002\/anie.201001686"},{"key":"7","doi-asserted-by":"crossref","unstructured":"7) Zhu Y., Liu X., Dong S., Zhou Y., Li W., Lin L., Feng X., Angew. Chem. Int. Ed.<\/i>, 53<\/b>, 1636\u20131640 (2014).","DOI":"10.1002\/anie.201308501"},{"key":"8","doi-asserted-by":"crossref","unstructured":"8) Li L., Sivaguru P., Han X., Karmakar S., Bi X., Org. Chem. Front.<\/i>, 10<\/b>, 1746\u20131753 (2023).","DOI":"10.1039\/D3QO00156C"},{"key":"9","doi-asserted-by":"crossref","unstructured":"9) Li M.-L., Yu J.-H., Li Y.-H., Zhu S.-F., Zhou Q.-L., Science<\/i>, 366<\/b>, 990\u2013994 (2019).","DOI":"10.1126\/science.aaw9939"},{"key":"10","doi-asserted-by":"crossref","unstructured":"10) Lee E. C., Fu G. C., J. Am. Chem. Soc.<\/i>, 129<\/b>, 12066\u201312067 (2007).","DOI":"10.1021\/ja074483j"},{"key":"11","doi-asserted-by":"crossref","unstructured":"11) Xu B., Zhu S.-F., Xie X.-L., Shen J.-J., Zhou Q.-L., Angew. Chem. Int. Ed.<\/i>, 50<\/b>, 11483\u201311486 (2011).","DOI":"10.1002\/anie.201105485"},{"key":"12","doi-asserted-by":"crossref","unstructured":"12) Arredondo V., Hiew S. C., Gutman E. S., Premachandra I. D. U. A., Van Vranken D. L., Angew. Chem. Int. Ed.<\/i>, 56<\/b>, 4156\u20134159 (2017).","DOI":"10.1002\/anie.201611845"},{"key":"13","doi-asserted-by":"crossref","unstructured":"13) Yang J., Ruan P., Yang W., Feng X., Liu X., Chem. Sci.<\/i> (Camb.), 10<\/b>, 10305\u201310309 (2019).","DOI":"10.1039\/C9SC03354H"},{"key":"14","doi-asserted-by":"crossref","unstructured":"14) Ford A., Miel H., Ring A., Slattery C. N., Maguire A. R., McKervey M. A., Chem. Rev.<\/i>, 115<\/b>, 9981\u201310080 (2015).","DOI":"10.1021\/acs.chemrev.5b00121"},{"key":"15","doi-asserted-by":"crossref","unstructured":"15) Hansen S. R., Spangler J. E., Hansen J. H., Davies H. M. L., Org. Lett.<\/i>, 14<\/b>, 4626\u20134629 (2012).","DOI":"10.1021\/ol3020754"},{"key":"16","doi-asserted-by":"crossref","unstructured":"16) Hu S., Wu J., Lu Z., Wang J., Tao Y., Jiang M., Chen F., J. Org. Chem.<\/i>, 86<\/b>, 3223\u20133231 (2021).","DOI":"10.1021\/acs.joc.0c02588"},{"key":"17","doi-asserted-by":"crossref","unstructured":"17) Stivanin M. L., Fernandes A. A. G., da Silva A. F., Okada C. Y. Jr., Jurberg I. D., Adv. Synth. Catal.<\/i>, 362<\/b>, 1106\u20131111 (2020).","DOI":"10.1002\/adsc.201901343"},{"key":"18","doi-asserted-by":"crossref","unstructured":"18) Guo W., Zhou Y., Xie H., Yue X., Jiang F., Huang H., Han Z., Sun J., Chem. Sci.<\/i> (Camb.), 14<\/b>, 843\u2013848 (2023).","DOI":"10.1039\/D2SC05149D"},{"key":"19","doi-asserted-by":"crossref","unstructured":"19) Mangion I. K., Nwamba I. K., Shevlin M., Huffman M. A., Org. Lett.<\/i>, 11<\/b>, 3566\u20133569 (2009).","DOI":"10.1021\/ol901298p"},{"key":"20","doi-asserted-by":"crossref","unstructured":"20) Mangion I. K., Weisel M., Tetrahedron Lett.<\/i>, 51<\/b>, 5490\u20135492 (2010).","DOI":"10.1016\/j.tetlet.2010.08.038"},{"key":"21","doi-asserted-by":"crossref","unstructured":"21) Chen G., Cai X., Zhang X., Fan X., J. Org. Chem.<\/i>, 87<\/b>, 9815\u20139828 (2022).","DOI":"10.1021\/acs.joc.2c00858"},{"key":"22","doi-asserted-by":"crossref","unstructured":"22) Xu X., Zavalij P. Y., Doyle M. P., Angew. Chem. Int. Ed.<\/i>, 51<\/b>, 9829\u20139833 (2012).","DOI":"10.1002\/anie.201203962"},{"key":"23","doi-asserted-by":"crossref","unstructured":"23) Shi B., Lewis W., Campbell I. B., Moody C. J., Org. Lett.<\/i>, 11<\/b>, 3686\u20133688 (2009).","DOI":"10.1021\/ol901502u"},{"key":"24","doi-asserted-by":"crossref","unstructured":"24) Le Goff G., Ouazzani J., Bioorg. Med. Chem.<\/i>, 22<\/b>, 6529\u20136544 (2014).","DOI":"10.1016\/j.bmc.2014.10.011"},{"key":"25","doi-asserted-by":"crossref","unstructured":"25) He H.-Y., Niikura H., Du Y.-L., Ryan K. S., Chem. Soc. Rev.<\/i>, 51<\/b>, 2991\u20133046 (2022).","DOI":"10.1039\/C7CS00458C"},{"key":"26","doi-asserted-by":"crossref","unstructured":"26) Licandro E., Perdicchia D., Eur. J. Org. Chem.<\/i>, 2004<\/b>, 665\u2013675 (2004).","DOI":"10.1002\/ejoc.200300416"},{"key":"27","doi-asserted-by":"crossref","unstructured":"27) Thota S., Rodrigues D. A., Pinheiro P. S. M., Lima L. M., Fraga G. A. M., Barreiro E. J., Bioorg. Med. Chem. Lett.<\/i>, 28<\/b>, 2797\u20132806 (2018).","DOI":"10.1016\/j.bmcl.2018.07.015"},{"key":"28","doi-asserted-by":"crossref","unstructured":"28) Fray M., Mathiron D., Pilard S., Lesur D., Abidi R., Barhoumi-Slimi T., Cragg P. J., Benazza M., Eur. J. Org. Chem.<\/i>, 2022<\/b>, 202101537 (2022).","DOI":"10.1002\/ejoc.202101537"},{"key":"29","doi-asserted-by":"crossref","unstructured":"29) Matunas R., Lai A. J., Lee C., Tetrahedron<\/i>, 61<\/b>, 6298\u20136308 (2005).","DOI":"10.1016\/j.tet.2005.03.105"},{"key":"30","doi-asserted-by":"crossref","unstructured":"30) Traor\u00e9 M., Doan N.-D., Lubell W. D., Org. Lett.<\/i>, 16<\/b>, 3583\u20133591 (2014).","DOI":"10.1021\/ol501586y"},{"key":"31","doi-asserted-by":"crossref","unstructured":"31) Lu B., Feng B., Ye H., Chen J.-R., Xiao W.-J., Org. Lett.<\/i>, 20<\/b>, 3473\u20133476 (2018).","DOI":"10.1021\/acs.orglett.8b01226"},{"key":"32","doi-asserted-by":"crossref","unstructured":"32) Du E. L., Borrel J., Waser J., Org. Lett.<\/i>, 24<\/b>, 6614\u20136618 (2022).","DOI":"10.1021\/acs.orglett.2c02625"},{"key":"33","doi-asserted-by":"crossref","unstructured":"33) Proulx C., Lubell W. D., Org. Lett.<\/i>, 12<\/b>, 2916\u20132919 (2010).","DOI":"10.1021\/ol100932m"},{"key":"34","doi-asserted-by":"crossref","unstructured":"34) Zhao G.-L., Shi M., Tetrahedron<\/i>, 61<\/b>, 7277\u20137288 (2005).","DOI":"10.1016\/j.tet.2005.04.071"},{"key":"35","doi-asserted-by":"crossref","unstructured":"35) Gembus V., Bonnet J.-J., Janin F., Bohn P., Levacher V., Bri\u00e8re J.-F., Org. Biomol. Chem.<\/i>, 8<\/b>, 3287\u20133293 (2010).","DOI":"10.1039\/c004704j"},{"key":"36","doi-asserted-by":"crossref","unstructured":"36) Cao S., Duan W., Tetrahedron Lett.<\/i>, 57<\/b>, 2390\u20132394 (2016).","DOI":"10.1016\/j.tetlet.2016.04.061"},{"key":"37","doi-asserted-by":"crossref","unstructured":"37) Matsuzaki H., Takeda N., Yasui M., Okazaki M., Suzuki S., Ueda M., Chem. Commun.<\/i> (Camb.), 57<\/b>, 12187\u201312190 (2021).","DOI":"10.1039\/D1CC05326D"},{"key":"38","doi-asserted-by":"crossref","unstructured":"38) Matsuzaki H., Takeda N., Yasui M., Ito Y., Konishi K., Ueda M., Org. Lett.<\/i>, 22<\/b>, 9249\u20139259 (2020).","DOI":"10.1021\/acs.orglett.0c03465"},{"key":"39","doi-asserted-by":"crossref","unstructured":"39) Ito Y., Ueda M., Takeda N., Miyata O., Chem. Eur. J.<\/i>, 22<\/b>, 2616\u20131619 (2016).","DOI":"10.1002\/chem.201504010"},{"key":"40","doi-asserted-by":"crossref","unstructured":"40) Ramirez E., Acc. Chem. Res.<\/i>, 1<\/b>, 168\u2013174 (1968).","DOI":"10.1021\/ar50006a002"},{"key":"41","doi-asserted-by":"crossref","unstructured":"41) Ramirez E., Pure Appl. Chem.<\/i>, 9<\/b>, 337\u2013369 (1964).","DOI":"10.1351\/pac196409020337"},{"key":"42","doi-asserted-by":"crossref","unstructured":"42) Osman F. H., EI-Samahy F. A., Chem. Rev.<\/i>, 102<\/b>, 629\u2013678 (2002).","DOI":"10.1021\/cr0000325"},{"key":"43","doi-asserted-by":"crossref","unstructured":"43) Liu Y., Sun F., He Z., Tetrahedron Lett.<\/i>, 59<\/b>, 4136\u20134148 (2018).","DOI":"10.1016\/j.tetlet.2018.10.023"},{"key":"44","doi-asserted-by":"crossref","unstructured":"44) Takeda N., Maeda R., Yasui M., Ueda M., Chem. Commun.<\/i> (Camb.), 60<\/b>, 172\u2013175 (2024).","DOI":"10.1039\/D3CC05522A"},{"key":"45","doi-asserted-by":"crossref","unstructured":"45) Miller E. J., Zhao W., Herr J. D., Radosevich A. T., Angew. Chem. Int. Ed.<\/i>, 51<\/b>, 10605\u201310609 (2012).","DOI":"10.1002\/anie.201205604"},{"key":"46","doi-asserted-by":"crossref","unstructured":"46) Liu R., Liu J., Cao J., Li R., Qiao Y., Gao W.-C., Org. Lett.<\/i>, 22<\/b>, 6922\u20136926 (2020).","DOI":"10.1021\/acs.orglett.0c02453"},{"key":"47","unstructured":"47) The reaction of ethyl pyruvate with hydrazone 2a<\/b> and P(NMe2<\/sub>)3<\/sub> gave corresponding N\u2013H insertion product in 17% yield."}],"container-title":["Chemical and Pharmaceutical Bulletin"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.jstage.jst.go.jp\/article\/cpb\/72\/4\/72_c24-00091\/_pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,12,14]],"date-time":"2024-12-14T03:32:00Z","timestamp":1734147120000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.jstage.jst.go.jp\/article\/cpb\/72\/4\/72_c24-00091\/_article"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,4,26]]},"references-count":47,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2024]]}},"URL":"https:\/\/doi.org\/10.1248\/cpb.c24-00091","relation":{},"ISSN":["0009-2363","1347-5223"],"issn-type":[{"value":"0009-2363","type":"print"},{"value":"1347-5223","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,4,26]]},"article-number":"c24-00091"}}