Selectfluor-Mediated Stereoselective [1 + 1 + 4 + 4] Dimerization of Styrylnaphthols

Autor:	Bo-Bo Gou, Jie Chen, Rui-Di Xue, Zi-Bo Wu, Hui Yang, Yibo Lei, Huai-Ri Sun, Ling Zhou
Rok vydání:	2019
Předmět:	010405 organic chemistry Stereochemistry Chemistry Organic Chemistry Intermolecular force 010402 general chemistry 01 natural sciences Biochemistry Cycloaddition 0104 chemical sciences chemistry.chemical_compound Intramolecular force Stereoselectivity Physical and Theoretical Chemistry Selectfluor
Zdroj:	Organic Letters. 21:9829-9835
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.9b03587
Popis:	Stereoselective [1 + 1 + 4 + 4] dimerization of 1-styrylnaphthols has been developed by using Selectfluor as the oxidant for the first time. The reaction was compatible with various functional groups, giving a class of ethanodinaphtho[b,f][1,5]dioxocines with novel 3D skeletons. DFT calculations indicate that this method merges an intriguing stereoselective intermolecular 1 + 1 radical coupling to construct a bridged C–C bond and then an intramolecular [4 + 4] formal cycloaddition of the in situ generated o-quinone methide intermediate.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2225f217a0a970456a401aa99b1e6649 https://doi.org/10.1021/acs.orglett.9b03587 Zobrazit plný text záznamu