{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,9]],"date-time":"2026-01-09T02:56:26Z","timestamp":1767927386212,"version":"3.49.0"},"reference-count":44,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2024,4,13]],"date-time":"2024-04-13T00:00:00Z","timestamp":1712966400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Hungarian Research Foundation","award":["NKFI K138871"],"award-info":[{"award-number":["NKFI K138871"]}]},{"name":"Hungarian Research Foundation","award":["TKP2021-EGA-32"],"award-info":[{"award-number":["TKP2021-EGA-32"]}]},{"name":"Ministry of Innovation and Technology of Hungary from the National Research, Development and Innovation Fund","award":["NKFI K138871"],"award-info":[{"award-number":["NKFI K138871"]}]},{"name":"Ministry of Innovation and Technology of Hungary from the National Research, Development and Innovation Fund","award":["TKP2021-EGA-32"],"award-info":[{"award-number":["TKP2021-EGA-32"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>A library of regioisomeric monoterpene-based aminodiols was synthesised and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The synthesis of the first type of aminodiols was achieved starting from (\u2212)-8,9-dihydroperillaldehyde via reductive amination, followed by Boc protection and dihydroxylation with the OsO4\/NMO system. Separation of formed stereoisomers resulted in a library of aminodiol diastereoisomers. The library of regioisomeric analogues was obtained starting from (\u2212)-8,9-dihydroperillic alcohol, which was transformed into a mixture of allylic trichloroacetamides via Overman rearrangement. Changing the protecting group to a Boc function, the protected enamines were subjected to dihydroxylation with the OsO4\/NMO system, leading to a 71:16:13 mixture of diastereoisomers, which were separated, affording the three isomers in isolated form. The obtained primary aminodiols were transformed into secondary derivatives. The regioselectivity of the ring closure of the N-benzyl-substituted aminodiols with formaldehyde was also investigated, resulting in 1,3-oxazines in an exclusive manner. To explain the stability difference between diastereoisomeric 1,3-oxazines, a series of comparative theoretical modelling studies was carried out. The obtained potential catalysts were applied in the reaction of aromatic aldehydes and diethylzinc with moderate to good enantioselectivities (up to 94% ee), whereas the opposite chiral selectivity was observed between secondary aminodiols and their ring-closed 1,3-oxazine analogues.<\/jats:p>","DOI":"10.3390\/ijms25084325","type":"journal-article","created":{"date-parts":[[2024,4,15]],"date-time":"2024-04-15T10:24:26Z","timestamp":1713176666000},"page":"4325","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Stereoselective Synthesis and Catalytical Application of Perillaldehyde-Based 3-Amino-1,2-diol Regioisomers"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0009-0003-4205-1738","authenticated-orcid":false,"given":"M\u00e1rton Benedek","family":"H\u00e1znagy","sequence":"first","affiliation":[{"name":"Institute of Pharmacognosy, University of Szeged, H-6720 Szeged, Hungary"},{"name":"Institute of Pharmaceutical Chemistry, Interdisciplinary Excellence Center, University of Szeged, E\u00f6tv\u00f6s utca 6, H-6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2107-7309","authenticated-orcid":false,"given":"Antal","family":"Cs\u00e1mpai","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, E\u00f6tv\u00f6s Lor\u00e1nd University, P.O. Box 32, H-1518 Budapest, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Imre","family":"Ugrai","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Chemistry, Interdisciplinary Excellence Center, University of Szeged, E\u00f6tv\u00f6s utca 6, H-6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Barnab\u00e1s","family":"Moln\u00e1r","sequence":"additional","affiliation":[{"name":"Department of Molecular and Analytical Chemistry, Interdisciplinary Excellence Centre, University of Szeged, D\u00f3m T\u00e9r 7-8, H-6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6744-7208","authenticated-orcid":false,"given":"Matti","family":"Haukka","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Jyv\u00e4skyl\u00e4, P.O. Box 35, 40351 Jyv\u00e4skyl\u00e4, Finland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2432-8409","authenticated-orcid":false,"given":"Zsolt","family":"Szakonyi","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Chemistry, Interdisciplinary Excellence Center, University of Szeged, E\u00f6tv\u00f6s utca 6, H-6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,4,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Berkessel, A., and Gr\u00f6ger, H. (2005). Asymmetric Organocatalysis\u2014From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH.","DOI":"10.1002\/3527604677"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Lin, G.-Q., You, Q.-D., and Cheng, J.-F. (2011). 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