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To address it, we herein report a synthetic methodology for preparing basket\u2010like cavitands comprised of three different aromatics as side arms with orthogonal esters at the rim for further functionalization. First, enantioenriched <jats:bold>A<\/jats:bold> (borochloronorbornene), <jats:bold>B<\/jats:bold> (iodobromonorbornene), and <jats:bold>C<\/jats:bold> (boronorbornene) building blocks were obtained by stereoselective syntheses. Second, consecutive <jats:bold>A<\/jats:bold>\u2010to\u2010<jats:bold>B<\/jats:bold> and then <jats:bold>AB<\/jats:bold>\u2010to\u2010<jats:bold>C<\/jats:bold> Suzuki\u2013Miyaura (SM) couplings were optimized to give enantioenriched <jats:bold>ABC<\/jats:bold> cavitand as the principal product. The robust synthetic protocol allowed us to prepare (a)\u2005an enantioenriched basket with three benzene sides and each holding either tBu, Et, or Me esters, (b)\u2005both enantiomers of a so\u2010called \u201cspiral staircase\u201d basket with benzene, naphthalene, and anthracene groups surrounding the inner space, and (c)\u2005a photo\u2010responsive basket bearing one anthracene and two benzene arms.<\/jats:p>","DOI":"10.1002\/anie.202110849","type":"journal-article","created":{"date-parts":[[2021,9,21]],"date-time":"2021-09-21T06:01:43Z","timestamp":1632204103000},"page":"25075-25081","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Enantioselective Construction of Modular and Asymmetric Baskets"],"prefix":"10.1002","volume":"60","author":[{"given":"Michael J.","family":"Gunther","sequence":"first","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry The Ohio State University  100 West 18<sup>th<\/sup> Avenue Columbus OH USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Radoslav Z.","family":"Pavlovi\u0107","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry The Ohio State University  100 West 18<sup>th<\/sup> Avenue Columbus OH USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tyler J.","family":"Finnegan","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry The Ohio State University  100 West 18<sup>th<\/sup> Avenue Columbus OH USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiuze","family":"Wang","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry The Ohio State University  100 West 18<sup>th<\/sup> Avenue Columbus OH USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7540-2387","authenticated-orcid":false,"given":"Jovica D.","family":"Badji\u0107","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry The Ohio State University  100 West 18<sup>th<\/sup> Avenue Columbus OH USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,10,21]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201408487"},{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201408487"},{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200200565"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200200565"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC05788F"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(90)90174-J"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11030-005-1314-x"},{"key":"e_1_2_6_6_1","first-page":"25","volume":"1","author":"Wittenberg J. 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