Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols
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...
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Beilstein-Institut
2021-05-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.17.80 |
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| author | Ákos Bajtel Mounir Raji Matti Haukka Ferenc Fülöp Zsolt Szakonyi |
| author_facet | Ákos Bajtel Mounir Raji Matti Haukka Ferenc Fülöp Zsolt Szakonyi |
| author_sort | Ákos Bajtel |
| collection | DOAJ |
| description | 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 (1<i>R</i>)-(−)-myrtenol (<b>10</b>). 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 CDCl<sub>3</sub>. |
| first_indexed | 2024-12-17T00:55:20Z |
| format | Article |
| id | doaj.art-e2d8a6aea0074704bf2fd70136504dd2 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T00:55:20Z |
| publishDate | 2021-05-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-e2d8a6aea0074704bf2fd70136504dd22022-12-21T22:09:37ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-05-0117198399010.3762/bjoc.17.801860-5397-17-80Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diolsÁkos Bajtel0Mounir Raji1Matti Haukka2Ferenc Fülöp3Zsolt Szakonyi4Department of Pharmacognosy, University of Szeged, Eötvös u. 6, Szeged, 6720, HungaryInstitute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, HungaryDepartment of Chemistry, University of Jyväskylä, POB 35, 40351 Jyväskylä, FinlandInstitute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, HungaryInstitute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, HungaryA 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 (1<i>R</i>)-(−)-myrtenol (<b>10</b>). 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 CDCl<sub>3</sub>.https://doi.org/10.3762/bjoc.17.802-amino-1,2-diolmonoterpeneoxazolidin-2-onestereoselectivetautomerism |
| spellingShingle | Ákos Bajtel Mounir Raji Matti Haukka Ferenc Fülöp Zsolt Szakonyi Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols Beilstein Journal of Organic Chemistry 2-amino-1,2-diol monoterpene oxazolidin-2-one stereoselective tautomerism |
| title | Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols |
| title_full | Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols |
| title_fullStr | Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols |
| title_full_unstemmed | Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols |
| title_short | Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols |
| title_sort | stereoselective synthesis and transformation of pinane based 2 amino 1 3 diols |
| topic | 2-amino-1,2-diol monoterpene oxazolidin-2-one stereoselective tautomerism |
| url | https://doi.org/10.3762/bjoc.17.80 |
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