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A Versatile Synthesis of Functionalized Pentahelicenes
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SYSNO ASEP 0353234 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title A Versatile Synthesis of Functionalized Pentahelicenes Author(s) Songis, Olivier (UOCHB-X)
Míšek, Jiří (UOCHB-X)
Schmid, Markus B. (UOCHB-X)
Kollárovič, Adrian (UOCHB-X)
Stará, Irena G. (UOCHB-X) RID, ORCID
Šaman, David (UOCHB-X) RID, ORCID
Císařová, I. (CZ)
Starý, Ivo (UOCHB-X) RID, ORCIDNumber of authors 8 Source Title Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 75, č. 20 (2010), s. 6889-6899Number of pages 11 s. Language eng - English Country US - United States Keywords functionalized pentahelicene ; synthesis ; Suzuki-Miyaura coupling Subject RIV CC - Organic Chemistry R&D Projects IAA400550916 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR) LC512 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000282604900017 DOI 10.1021/jo1013977 Annotation A general synthetic methodology for the preparation of functionalized (hetero)helicenes has been developed. It employs the sequence of a double propargyl organometallics (Li, Mg, Ga/In) addition to a tolan-2,2'-dialdehyde-type intermediate, a cobalt-catalyzed [2 + 2 + 2] cycloisomerization of a triyne intermediate, and a double silica gel-assisted acetic acid elimination to receive pentahelicene followed by palladium catalyzed Suzuki-Miyaura coupling. 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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