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Model synthesis of six-membered carbocyclic spironucleosides
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SYSNO ASEP 0351445 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Model synthesis of six-membered carbocyclic spironucleosides Author(s) Nencka, Radim (UOCHB-X) RID, ORCID
Hřebabecký, Hubert (UOCHB-X) RID, ORCID
Dračínský, Martin (UOCHB-X) RID, ORCIDNumber of authors 3 Source Title Collection of Czechoslovak Chemical Communications. - : Ústav organické chemie a biochemie AV ČR, v. v. i. - ISSN 0010-0765
Roč. 75, č. 12 (2010), s. 1259-1272Number of pages 14 s. Language eng - English Country CZ - Czech Republic Keywords spironucleosides ; carbocyclic ; Bucherer-Bergs reaction ; Michaels addition ; tandem reaction Subject RIV CC - Organic Chemistry R&D Projects 1M0508 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000285770100004 DOI 10.1135/cccc2010103 Annotation Model study focusing on the synthesis of carbocyclic spironucleosides is presented. Hydantoin base was built on the easily accessible ketone precursors by Bucherer–Bergs reaction. On saturated substrates the reaction proceeded smoothly. On α,β-unsaturated ketones, however, the Bucherer–Bergs reaction competed with Michael addition of cyanide ion. We showed that the equilibrium of the reaction could be significantly shifted depending on the applied reaction conditions. Significant diastereoselectivity was observed for tandem Michael addition/Bucherer–Bergs reaction. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2011
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