{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T14:47:24Z","timestamp":1792075644533,"version":"4.4.0"},"reference-count":39,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T00:00:00Z","timestamp":1790985600000},"content-version":"vor","delay-in-days":2,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T00:00:00Z","timestamp":1790812800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["EXC\u20102094\u2010390783311"],"award-info":[{"award-number":["EXC\u20102094\u2010390783311"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["521256690\u2010TRR 392"],"award-info":[{"award-number":["521256690\u2010TRR 392"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2026,10]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    The Soai reaction is a unique example of self\u2010amplifying asymmetric autocatalysis, in which a chiral zinc alkoxide not only promotes its own formation from pyridine\u20103\u2010carbaldehydes and pyrimidine\u20105\u2010carbaldehydes by alkylation with diisopropylzinc but also amplifies the enantiomeric excess of the added nonracemic alcohol. Both the asymmetric autocatalysis and the positive nonlinear effect have been attributed to equilibria involving the zinc alkoxide product, including dimerization and hemiacetalate formation with the substrate aldehyde. Hemiacetal formation is therefore of central importance for the efficiency of the autocatalytic cycle. Here, we report kinetic investigations of the dynamic hemiacetal formation of Soai aldehydes, showing a correlation of hemiacetal formation rates with autocatalytic reactivity. Hemiacetal formation with a series of alcohols was studied by\n                    <jats:sup>1<\/jats:sup>\n                    H NMR spectroscopy and temperature\u2010dependent dynamic HPLC (DHPLC), providing mechanistic insight into the stereodynamics governing this key equilibrium. The Gibbs free activation energy \u0394\n                    <jats:italic>G<\/jats:italic>\n                    <jats:sup>\u01c2<\/jats:sup>\n                    for the formation of hemiacetals with isopropanol for pyridine\u20103\u2010carbaldehydes is in the range between 94.6 and 95.5\u2009kJ\/mol and for pyrimidine\u20105\u2010carbaldehydes it is between 85.9 and 88.4\u2009kJ\/mol.\n                  <\/jats:p>","DOI":"10.1002\/chir.70152","type":"journal-article","created":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T09:11:55Z","timestamp":1791018715000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Stereodynamics of Hemiacetal Formation in Pyridine\u20103\u2010Carbaldehyde and Pyrimidine\u20105\u2010Carbaldehyde Derivatives: Implications for the Soai Reaction"],"prefix":"10.1002","volume":"38","author":[{"given":"Patrick","family":"M\u00f6hler","sequence":"first","affiliation":[{"name":"Department of Chemistry Ludwig\u2010Maximilians\u2010University Munich  Munich Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander F.","family":"Siegle","sequence":"additional","affiliation":[{"name":"Department of Chemistry Ludwig\u2010Maximilians\u2010University Munich  Munich Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3594-5181","authenticated-orcid":false,"given":"Oliver","family":"Trapp","sequence":"additional","affiliation":[{"name":"Department of Chemistry Ludwig\u2010Maximilians\u2010University Munich  Munich 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