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Ring-Opening Reactions of Aziridines Fused to a Conformationally Locked Tetrahydropyran Ring
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SYSNO ASEP 0333114 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Ring-Opening Reactions of Aziridines Fused to a Conformationally Locked Tetrahydropyran Ring Title Štěpení aziridinového cyklu anelovaného ke konformačně fixovanému tetrahydropyranovému cyklu Author(s) Karban, Jindřich (UCHP-M) RID, ORCID, SAI
Kroutil, J. (CZ)
Buděšínský, Miloš (UOCHB-X) RID, ORCID
Sýkora, Jan (UCHP-M) RID, ORCID, SAI
Císařová, I. (CZ)Source Title European Journal of Organic Chemistry - ISSN 1434-193X
Roč. 2009, č. 36 (2009), s. 6399-6406Number of pages 8 s. Language eng - English Country DE - Germany Keywords aziridines ; carbohydrates ; regioselectivity Subject RIV CF - Physical ; Theoretical Chemistry R&D Projects IAA400720703 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR) IAA400720706 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR) CEZ AV0Z40720504 - UCHP-M (2005-2011) AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000273187700017 DOI DOI:10.1002/ejoc200900762 Annotation 1,6-Anhydro-2,3,4-trideoxy-2,3-(tosylepimino)-β-D-hexopyranoses 1 and 2 underwent aziridine ring-opening reactions with halides and other heteroatom-centered nucleophiles. Ribo-epimine 1 provided trans-diaxial and cis products. The lyxo-epimine 2 gave trans-diaxial and trans-diequatorial products, depending upon the reaction conditions (acid cleavage versus base cleavage) and the nucleophile (hard nucleophiles versus soft ones). These results have been rationalized by assuming that both SN2 and borderline SN2 cleavage mechanisms are operative. Workplace Institute of Chemical Process Fundamentals Contact Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227 Year of Publishing 2010
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