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dc.contributor.authorBajtel, Ákos
dc.contributor.authorRaji, Mounir
dc.contributor.authorHaukka, Matti
dc.contributor.authorFülöp, Ferenc
dc.contributor.authorSzakonyi, Zsolt
dc.date.accessioned2021-05-11T06:46:23Z
dc.date.available2021-05-11T06:46:23Z
dc.date.issued2021
dc.identifier.citationBajtel, Á., Raji, M., Haukka, M., Fülöp, F., & Szakonyi, Z. (2021). Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols. <i>Beilstein Journal of Organic Chemistry</i>, <i>17</i>, 983-990. <a href="https://doi.org/10.3762/bjoc.17.80" target="_blank">https://doi.org/10.3762/bjoc.17.80</a>
dc.identifier.otherCONVID_68795853
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/75441
dc.description.abstractA library of pinane-based 2-amino-1,3-diols was synthesised in a stereoselective manner. Isopinocarveol prepared from (−)-α-pinene was converted into condensed oxazolidin-2-one in two steps by carbamate formation followed by a stereoselective aminohydroxylation process. The relative stereochemistry of the pinane-fused oxazolidin-2-one was determined by 2D NMR and X-ray spectroscopic techniques. The regioisomeric spiro-oxazolidin-2-one was prepared in a similar way starting from the commercially available (1R)-(−)-myrtenol (10). The reduction or alkaline hydrolysis of the oxazolidines, followed by reductive alkylation resulted in primary and secondary 2-amino-1,3-diols, which underwent a regioselective ring closure with formaldehyde or benzaldehyde delivering pinane-condensed oxazolidines. During the preparation of 2-phenyliminooxazolidine, an interesting ring–ring tautomerism was observed in CDCl3.en
dc.format.mimetypeapplication/pdf
dc.language.isoeng
dc.publisherBeilstein Institut
dc.relation.ispartofseriesBeilstein Journal of Organic Chemistry
dc.rightsCC BY 4.0
dc.subject.other2-amino-1,2-diol
dc.subject.othermonoterpene
dc.subject.otheroxazolidin-2-one
dc.subject.otherstereoselective
dc.subject.othertautomerism
dc.titleStereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202105112726
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineEpäorgaaninen kemiafi
dc.contributor.oppiaineEpäorgaaninen ja analyyttinen kemiafi
dc.contributor.oppiaineInorganic Chemistryen
dc.contributor.oppiaineInorganic and Analytical Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.format.pagerange983-990
dc.relation.issn2195-951X
dc.relation.volume17
dc.type.versionpublishedVersion
dc.rights.copyright© 2021 the Authors
dc.rights.accesslevelopenAccessfi
dc.subject.ysomonoterpeenit
dc.subject.ysotautomeria
dc.subject.ysokemiallinen synteesi
dc.subject.ysoorgaaniset yhdisteet
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p20942
jyx.subject.urihttp://www.yso.fi/onto/yso/p10131
jyx.subject.urihttp://www.yso.fi/onto/yso/p8468
jyx.subject.urihttp://www.yso.fi/onto/yso/p3841
dc.rights.urlhttps://creativecommons.org/licenses/by/4.0/
dc.relation.doi10.3762/bjoc.17.80
jyx.fundinginformationWe are grateful for financial support from the EU-funded Hungarian grant GINOP-2.3.2-15-2016-00012, Ministry of Human Capacities, Hungary grant 20391-3/2018/FEKUSTRAT, Hungarian Research Foundation (OTKA No. K 115731), and Nóra Korom-Tóth for her experimental assistance.
dc.type.okmA1


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