Modified Synthesis of Heptahelicene and Its Resolution Into Single Enantiomers

Autor:	Stephen G. Urquhart, Irena G. Stará, Petr Sehnal, Ivo Stary, Edwige Otero, Zuzana Alexandrová, David Šaman
Rok vydání:	2006
Předmět:	Resolution (mass spectrometry) Chemistry Resolution (electron density) Enantioselective synthesis General Medicine General Chemistry Combinatorial chemistry Medicinal chemistry Catalysis Chiral column chromatography chemistry.chemical_compound Cycloisomerization Acetylene Enantiomer
Zdroj:	Collection of Czechoslovak Chemical Communications. 71:1256-1264
ISSN:	1212-6950 0010-0765
Popis:	A practical synthesis of racemic heptahelicene has been develeped being based on key [2+2+2] cycloisomerization of bis[2-(but-3-yn-1-yl)-1-naphthyl]acetylene under CpCo(CO)2/PPh3 or CpCo(C2H4)2 catalysis. The application of the Ni(cod)2 catalyst with (-)-(Sa)-(2'-methoxy-1,1'-binaphthalen-2-yl)diphenylphosphane resulted in enantioselective triyne cyclization to provide (+)-7,8,11,12-tetrahydroheptahelicene in 40% ee. Optically pure (-)-(M)- and optically highly enriched (+)-(P)-heptahelicene were obtained on a milligram scale by resolution of racemate by chiral HPLC on a semipreparative Whelk-O1 column.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8887d3b4aa2350cc1d045831de95cdec https://doi.org/10.1135/cccc20061256 Zobrazit plný text záznamu