We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Fe‐catalyzed hydrohalogenative cyclization of cyclohexadienone‐containing enynes.
- Authors
Hong, Ya‐Chun; Santhoshkumar, Rajagopal; Cheng, Chien‐Hong
- Abstract
A Fe‐catalyzed hydrohalogenative cyclization of cyclohexadienone‐containing 1,n‐enynes to give three different types of compounds is discussed. 1,6‐enynes with a stoichiometric amount of FeX3 provided cis‐hydrobenzofurans with moderate stereoselectivity, whereas the reaction with TMSX (X = Cl, Br) as the halide source in the presence of Fe catalyst improved the stereoselectivity of halide addition highly. The alkyl vs aryl shows difference that the reaction of 1,6‐enynes bearing an alkylethynyl group gave meta alkenated phenols (2 examples) whereas a similar reaction of 1,6‐enynes with an arylethynyl group delivered only cis‐hydrobenzofurans (12 examples). 1,7‐enynes afforded tricyclic products (4 examples). The different reactivity of 1,6‐ and 1,7‐enynes is probably influenced by the formation of a six‐membered chair‐like intermediate in 1,6‐enynes.
- Subjects
STEREOSELECTIVE reactions; ENYNES; PHENOLS; HALIDES; CATALYSTS; IRON compounds
- Publication
Journal of the Chinese Chemical Society, 2019, Vol 66, Issue 9, p1221
- ISSN
0009-4536
- Publication type
Article
- DOI
10.1002/jccs.201900292