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By conformational search, it was confirmed that catalyst 1 and its enamine intermediate adopted a dominant conformation with a \u03b2I structure stabilized by a C10 H-bond between the C\u2550O of d-Pro1 and C-terminal NH2 proton and by an additional H-bond between the side chain and the backbone of Glu3. This \u03b2I turn structure was conserved all along the catalytic cycle. Consistently with the kinetic studies, the C\u2013C bond formation between the enamine and electrophile was also confirmed as the rate-determining step. The stereoselectivity results from a re \u2192 re prochiral approach of enamine and \u03b2-nitrostyrene with a gauche\u2013 orientation of the double bonds. Although it was suggested as the possible formation of dihydrooxazine oxide species, this process was confirmed to be kinetically less accessible than the formation of acyclic nitronate. In particular, our calculated results supported that the carboxylic acid group of Glu3 in 1 played a central role by acting as general acid\/base all along the catalytic cycle and orienting the asymmetric C\u2013C bond formation.<\/jats:p>","DOI":"10.1021\/acsomega.9b00465","type":"journal-article","created":{"date-parts":[[2019,5,30]],"date-time":"2019-05-30T12:11:47Z","timestamp":1559218307000},"page":"8862-8873","source":"Crossref","is-referenced-by-count":9,"title":["Organocatalytic Asymmetric Addition of Aldehyde to\nNitroolefin by H-\n                    <scp>d<\/scp>\n                    -Pro-Pro-Glu-NH2: A Mechanistic Study"],"prefix":"10.1021","volume":"4","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9437-9765","authenticated-orcid":true,"given":"Ludovic T.","family":"Maillard","sequence":"first","affiliation":[{"name":"Institut des Biomole\u0301cules Max Mousseron, UMR CNRS-UM-ENSCM 5247, UFR des Sciences Pharmaceutiques et Biologiques , 15 Avenue Charles Flahault , ,","place":["Montpellier Cedex 5, France, 34093"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hae Sook","family":"Park","sequence":"additional","affiliation":[{"name":"Cheju Halla University , , ,","place":["Cheju, Republic of Korea, 63092"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2200-8922","authenticated-orcid":true,"given":"Young Kee","family":"Kang","sequence":"additional","affiliation":[{"name":"Chungbuk National University , , , ,","place":["Cheongju, Chungbuk, Republic of Korea, 28644"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2019,5,22]]},"reference":[{"key":"2026090317510197800_cit1a","doi-asserted-by":"crossref","DOI":"10.1002\/3527604677","volume-title":"Asymmetric\nOrganocatalysis from Biomimetic Concepts to Applications in Asymmetric\nSynthesis","author":"Berkessel","year":"2005"},{"key":"2026090317510197800_cit1b","doi-asserted-by":"publisher","first-page":"8","DOI":"10.1016\/j.drudis.2006.11.004","article-title":"Enantioselective\nOrganocatalysis","volume":"12","author":"Gaunt","year":"2007","journal-title":"Drug Discov. 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