{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,18]],"date-time":"2026-03-18T04:21:21Z","timestamp":1773807681496,"version":"3.50.1"},"reference-count":43,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2020,3,27]],"date-time":"2020-03-27T00:00:00Z","timestamp":1585267200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100007595","name":"Belarusian Republican Foundation for Fundamental Research","doi-asserted-by":"publisher","award":["Kh19RM-002"],"award-info":[{"award-number":["Kh19RM-002"]}],"id":[{"id":"10.13039\/100007595","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002261","name":"Russian Foundation for Basic Research","doi-asserted-by":"publisher","award":["19-53-04005 Bel_mol_a"],"award-info":[{"award-number":["19-53-04005 Bel_mol_a"]}],"id":[{"id":"10.13039\/501100002261","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemCatChem"],"published-print":{"date-parts":[[2020,5,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A range of heterogeneous \u2010SO<jats:sub>3<\/jats:sub>H functionalized catalysts including carbon and halloysite nanotubes, commercial K10 clay, Amberlyst\u201015 etc. was investigated for the first time using as a model the Prins\u2010Ritter reaction of (\u2212)\u2010isopulegol with benzaldehyde and acetonitrile producing 4\u2010amido derivatives of octahydro\u20102<jats:italic>H<\/jats:italic>\u2010chromenes (as (S)\u2010 and (<jats:italic>R<\/jats:italic>)\u2010diastereomers). A strong effect of water addition prior the reaction on the overall selectivity and the ratio of isomers in the case of heterogeneous and homogeneous (<jats:italic>p<\/jats:italic>\u2010toluenesulfonic acid) catalysis was found for the first time. The yield of the (<jats:italic>R<\/jats:italic>)\u2010diastereomer sharply increased with increasing amount of added water, while the <jats:italic>S<\/jats:italic>\u2010isomer prevailed with a minimum amount of added water. Experimental results and DFT calculations clearly indicate a kinetic control for <jats:italic>R<\/jats:italic>\u2010amide formation. Typically synthesis of 4\u2010amidooctahydro\u20102<jats:italic>H<\/jats:italic>\u2010chromenes requires subzero temperatures and toxic catalysts, which were avoided in the current work. Nevertheless, the yield of the desired products (up to 83\u2009%) at 30\u2009\u00b0C after water addition exceeded the values reported previously. Thus, adding water is a simple and a very effective method for controlling both the yield and stereoselectivity of the Prins\u2010Ritter reaction products under mild conditions.<\/jats:p>","DOI":"10.1002\/cctc.202000070","type":"journal-article","created":{"date-parts":[[2020,2,5]],"date-time":"2020-02-05T12:14:02Z","timestamp":1580904842000},"page":"2605-2609","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Stereoselectivity Inversion by Water Addition in the \u2212SO<sub>3<\/sub>H\u2010catalyzed Tandem Prins\u2010Ritter Reaction for Synthesis of 4\u2010amidotetrahydropyran Derivatives"],"prefix":"10.1002","volume":"12","author":[{"given":"Alexander Yu.","family":"Sidorenko","sequence":"first","affiliation":[{"name":"\u00c5bo Akademi University  Biskopsgatan 8 20500 Turku\/\u00c5bo Finland"},{"name":"Institute of Chemistry of New Materials of National Academy of Sciences of Belarus  Skaryna str. 36 220141 Minsk Belarus"}]},{"given":"Nikolai S.","family":"Li\u2010Zhulanov","sequence":"additional","affiliation":[{"name":"\u00c5bo Akademi University  Biskopsgatan 8 20500 Turku\/\u00c5bo Finland"},{"name":"Novosibirsk Institute of Organic Chemistry  Lavrentjev av. 9 630090 Novosibirsk Russia"},{"name":"Novosibirsk State University  Pirogova st. 1 630090 Novosibirsk Russia"}]},{"given":"P\u00e4ivi","family":"M\u00e4ki\u2010Arvela","sequence":"additional","affiliation":[{"name":"\u00c5bo Akademi University  Biskopsgatan 8 20500 Turku\/\u00c5bo Finland"}]},{"given":"Thomas","family":"Sandberg","sequence":"additional","affiliation":[{"name":"\u00c5bo Akademi University  Biskopsgatan 8 20500 Turku\/\u00c5bo Finland"}]},{"given":"Anna V.","family":"Kravtsova","sequence":"additional","affiliation":[{"name":"Institute of Chemistry of New Materials of National Academy of Sciences of Belarus  Skaryna str. 36 220141 Minsk Belarus"}]},{"given":"Andreia F.","family":"Peixoto","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE Departamento de Qu\u00edmica e Bioqu\u00edmica Faculdade de Ci\u00eancias Universidade do Porto  Rua do Campo Alegre s\/n 4169-007 Porto Portugal"}]},{"given":"Cristina","family":"Freire","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE Departamento de Qu\u00edmica e Bioqu\u00edmica Faculdade de Ci\u00eancias Universidade do Porto  Rua do Campo Alegre s\/n 4169-007 Porto Portugal"}]},{"given":"Konstantin P.","family":"Volcho","sequence":"additional","affiliation":[{"name":"Novosibirsk Institute of Organic Chemistry  Lavrentjev av. 9 630090 Novosibirsk Russia"},{"name":"Novosibirsk State University  Pirogova st. 1 630090 Novosibirsk Russia"}]},{"given":"Nariman F.","family":"Salakhutdinov","sequence":"additional","affiliation":[{"name":"Novosibirsk Institute of Organic Chemistry  Lavrentjev av. 9 630090 Novosibirsk Russia"},{"name":"Novosibirsk State University  Pirogova st. 1 630090 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