Synthesis of Cyclophanes via an Intermolecular Pd-Catalyzed Enyne−Diyne Cross-Benzannulation Approach

Autor:	Yoshinori Yamamoto, Norie Tsuboya, Vladimir Gevorgyan
Rok vydání:	2001
Předmět:	Olefin fiber chemistry.chemical_compound chemistry Enyne Stereochemistry Intramolecular force Organic Chemistry Intermolecular force Moiety Catalysis Cyclophane
Zdroj:	The Journal of Organic Chemistry. 66:2743-2746
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo0016531
Popis:	Several novel types of cyclophanes were efficiently synthesized via an intermolecular palladium-catalyzed cross-benzannulation of cyclic enynes and diynes. These types of cyclophanes are not accessible through an intramolecular mode of the homo-benzannulation protocol, reported previously. Cyclic reactants (enynes and diynes) were readily prepared in reasonable yields from commercially available materials using known procedures. The fact that the cyclic Z-enyne 29, in contrast to its E-counterpart, underwent benzannulation to produce the cyclophane 28 brought additional support for the necessity of having an E-hydrogen atom at the terminal olefin moiety of nonactivated enynes, which was found previously in the benzannulation of the acyclic susbstrates.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::137fd9661a9a82b5f6dcf2f7b9802c48 https://doi.org/10.1021/jo0016531 Zobrazit plný text záznamu