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The method was evaluated across 61 examples spanning structurally diverse linear and cyclic enones, including variation in aryl and heteroaryl substitution, alkyl substitution, ring size, and cyclic acceptor class. The resulting aza-Michael adducts were further utilized as synthetic intermediates for the preparation of biologically relevant motifs, including enantioenriched divergent cyclic 1,3-amino alcohols. The synthetic utility of the method was further demonstrated through the preparation of a key intermediate en route to N14-desacetoxytubulysin H. Mechanistic studies, including control experiments, 1H NMR titration studies, and DFT calculations, are consistent with a working bifunctional dual-organization model involving cooperative catalyst\u2013substrate interactions.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01696","type":"journal-article","created":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T22:01:51Z","timestamp":1790114511000},"page":"13228-13253","source":"Crossref","is-referenced-by-count":0,"title":["An Efficient Platform\nfor Enantioselective\n                    <i>aza<\/i>\n                    -Michael Addition to Both\nLinear and Cyclic Enones"],"prefix":"10.1021","volume":"91","author":[{"given":"Jaeyong","family":"Lee","sequence":"first","affiliation":[{"name":"Duksung Women\u2019s University , , ,","place":["Seoul, Republic of Korea, 01369"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"So Young","family":"Jang","sequence":"additional","affiliation":[{"name":"Seoul National University , , ,","place":["Seoul, Republic of Korea, 08826"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9645-8221","authenticated-orcid":true,"given":"Hyeung-geun","family":"Park","sequence":"additional","affiliation":[{"name":"Seoul National University , , ,","place":["Seoul, Republic of Korea, 08826"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,22]]},"reference":[{"issue":"9","key":"2026100208064032800_cit1","doi-asserted-by":"publisher","first-page":"1227","DOI":"10.1007\/s00726-020-02887-4","article-title":"Tailor-made amino acid-derived pharmaceuticals\napproved by the FDA in 2019","volume":"52","author":"Yin","year":"2020","journal-title":"Amino Acids"},{"key":"2026100208064032800_cit2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2021.113448","article-title":"Tailor-made amino acids\nin the design of small-molecule blockbuster\ndrugs","volume":"220","author":"Han","year":"2021","journal-title":"Eur. 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See supporting\ninformation for details."},{"key":"2026100208064032800_cit41","unstructured":"CCDC-2129351 ((1S,3R)-20)\nThe crystal structure of (1S,3R)-20 was visualized using CYLview20."},{"issue":"24","key":"2026100208064032800_cit42","doi-asserted-by":"publisher","first-page":"5567","DOI":"10.1021\/ol902320w","article-title":"First total synthesis of tubulysin\nB","volume":"11","author":"Pando","year":"2009","journal-title":"Org. Lett."},{"issue":"6","key":"2026100208064032800_cit43","doi-asserted-by":"publisher","first-page":"1530","DOI":"10.1021\/jm701321p","article-title":"Cytotoxic\nsimplified tubulysin analogues","volume":"51","author":"Raghavan","year":"2008","journal-title":"J. Med. Chem."},{"issue":"8","key":"2026100208064032800_cit44","doi-asserted-by":"publisher","first-page":"1605","DOI":"10.1021\/ol070415q","article-title":"Total synthesis of\nN 14-desacetoxytubulysin H","volume":"9","author":"Wipf","year":"2007","journal-title":"Org. 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