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We present the tripeptide H\u2010Pro\u2010Pro\u2010Asp\u2010NHC<jats:sub>12<\/jats:sub>H<jats:sub>25<\/jats:sub> as a catalyst for conjugate addition reactions between aldehydes and C\u2010substituted maleimides to form succinimides with three contiguous stereogenic centers in high yields and stereoselectivities. The peptidic catalyst is so chemoselective that no protecting group is needed at the imide nitrogen of the maleimides. Derivatization of the succinimides was straightforward and provided access to chiral pyrrolidines, lactones, and lactams. Kinetic studies, including a Hammett plot, provided detailed insight into the reaction mechanism.<\/jats:p>","DOI":"10.1002\/chem.202200215","type":"journal-article","created":{"date-parts":[[2022,1,28]],"date-time":"2022-01-28T10:00:00Z","timestamp":1643364000000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Peptide\u2010Catalyzed Stereoselective Conjugate Addition Reaction of Aldehydes to <i>C<\/i>\u2010Substituted Maleimides"],"prefix":"10.1002","volume":"28","author":[{"given":"Greta","family":"Vastakaite","sequence":"first","affiliation":[{"name":"Laboratory of Organic Chemistry ETH Z\u00fcrich  Vladimir-Prelog-Weg 3 8093 Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudio E.","family":"Gr\u00fcnenfelder","sequence":"additional","affiliation":[{"name":"Laboratory of Organic Chemistry ETH Z\u00fcrich  Vladimir-Prelog-Weg 3 8093 Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3075-5741","authenticated-orcid":false,"given":"Helma","family":"Wennemers","sequence":"additional","affiliation":[{"name":"Laboratory of Organic Chemistry ETH Z\u00fcrich  Vladimir-Prelog-Weg 3 8093 Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,2,28]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"For reviews see:"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2020.104557"},{"key":"e_1_2_3_3_2","first-page":"8","volume":"6","author":"Patil M. 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