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They contain elongated linear structures with three contiguous C=C bonds and sterically unhindered \u03b1\u2010carbon atoms. These structural features make it difficult to develop enantioselective reactions for these intermediates. Here we disclose the first carbene\u2010catalyzed highly enantioselective addition reactions of azolium cumulenolates. The reaction starts with alkynals as the precursors for azolium cumulenolate intermediates that undergo enantioselective addition to activated ketones. From the same set of substrates, both allene and spirooxindole products can be obtained with high yields and excellent enantioselectivities. The allene moieties in our optically enriched products carry rich reactivities and can be transformed to diverse molecules. The spirooxindole scaffolds in our products are important structural motifs in natural products and medicines.<\/jats:p>","DOI":"10.1002\/anie.202102177","type":"journal-article","created":{"date-parts":[[2021,4,9]],"date-time":"2021-04-09T06:50:09Z","timestamp":1617951009000},"page":"14817-14823","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":33,"title":["Access to Allene\u2010Containing Molecules via Enantioselective Reactions of Azolium Cumulenolate Intermediates"],"prefix":"10.1002","volume":"60","author":[{"given":"Yongtao","family":"Xie","sequence":"first","affiliation":[{"name":"International Joint Research Center for Molecular Science College of Chemistry and Environmental Engineering College of Physics and Optoelectronic Engineering Shenzhen University  Shenzhen 518060 China"},{"name":"Division of Chemistry &amp; Mathematical Science School of Physical &amp; Mathematical Sciences Nanyang Technological University  Singapore 637371 Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xing","family":"Yang","sequence":"additional","affiliation":[{"name":"Division of Chemistry &amp; Mathematical Science School of Physical &amp; Mathematical Sciences Nanyang Technological University  Singapore 637371 Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jun","family":"Xu","sequence":"additional","affiliation":[{"name":"College of Pharmacy Guizhou University of Traditional Chinese Medicine  Guiyang 550025 China"},{"name":"Division of Chemistry &amp; Mathematical Science School of Physical &amp; Mathematical Sciences Nanyang Technological University  Singapore 637371 Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huifang","family":"Chai","sequence":"additional","affiliation":[{"name":"College of Pharmacy Guizhou University of Traditional Chinese Medicine  Guiyang 550025 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Shenzhen 518060 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuan","family":"Gao","sequence":"additional","affiliation":[{"name":"International Joint Research Center for Molecular Science College of Chemistry and Environmental Engineering College of Physics and Optoelectronic Engineering Shenzhen University  Shenzhen 518060 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhichao","family":"Jin","sequence":"additional","affiliation":[{"name":"Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering Key Laboratory of Green Pesticide and Agricultural Bioengineering Ministry of Education Guizhou University Huaxi District  Guiyang 550025 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0573-257X","authenticated-orcid":false,"given":"Yonggui Robin","family":"Chi","sequence":"additional","affiliation":[{"name":"Laboratory Breeding Base of Green Pesticide and Agricultural 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