dc.contributor.author | Bajtel, Ákos | |
dc.contributor.author | Raji, Mounir | |
dc.contributor.author | Haukka, Matti | |
dc.contributor.author | Fülöp, Ferenc | |
dc.contributor.author | Szakonyi, Zsolt | |
dc.date.accessioned | 2021-05-11T06:46:23Z | |
dc.date.available | 2021-05-11T06:46:23Z | |
dc.date.issued | 2021 | |
dc.identifier.citation | Bajtel, 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.other | CONVID_68795853 | |
dc.identifier.uri | https://jyx.jyu.fi/handle/123456789/75441 | |
dc.description.abstract | A 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.mimetype | application/pdf | |
dc.language.iso | eng | |
dc.publisher | Beilstein Institut | |
dc.relation.ispartofseries | Beilstein Journal of Organic Chemistry | |
dc.rights | CC BY 4.0 | |
dc.subject.other | 2-amino-1,2-diol | |
dc.subject.other | monoterpene | |
dc.subject.other | oxazolidin-2-one | |
dc.subject.other | stereoselective | |
dc.subject.other | tautomerism | |
dc.title | Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols | |
dc.type | article | |
dc.identifier.urn | URN:NBN:fi:jyu-202105112726 | |
dc.contributor.laitos | Kemian laitos | fi |
dc.contributor.laitos | Department of Chemistry | en |
dc.contributor.oppiaine | Epäorgaaninen kemia | fi |
dc.contributor.oppiaine | Epäorgaaninen ja analyyttinen kemia | fi |
dc.contributor.oppiaine | Inorganic Chemistry | en |
dc.contributor.oppiaine | Inorganic and Analytical Chemistry | en |
dc.type.uri | http://purl.org/eprint/type/JournalArticle | |
dc.type.coar | http://purl.org/coar/resource_type/c_2df8fbb1 | |
dc.description.reviewstatus | peerReviewed | |
dc.format.pagerange | 983-990 | |
dc.relation.issn | 2195-951X | |
dc.relation.volume | 17 | |
dc.type.version | publishedVersion | |
dc.rights.copyright | © 2021 the Authors | |
dc.rights.accesslevel | openAccess | fi |
dc.subject.yso | monoterpeenit | |
dc.subject.yso | tautomeria | |
dc.subject.yso | kemiallinen synteesi | |
dc.subject.yso | orgaaniset yhdisteet | |
dc.format.content | fulltext | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p20942 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p10131 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p8468 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p3841 | |
dc.rights.url | https://creativecommons.org/licenses/by/4.0/ | |
dc.relation.doi | 10.3762/bjoc.17.80 | |
jyx.fundinginformation | We 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.okm | A1 | |