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Ni(ClO 4 ) 2 ‐Catalyzed Friedel–Crafts Reaction of Coumarin‐Fused Donor–Acceptor Cyclopropanes with Indoles: Stereoselective Synthesis of trans ‐3,4‐Disubstituted‐3,4‐dihydrocoumarins
Author(s) -
Lee Jusung,
Ko Kwang Min,
Kim SungGon
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800669
Subject(s) - chemistry , friedel–crafts reaction , stereoselectivity , lewis acids and bases , catalysis , coumarin , acceptor , organic chemistry , medicinal chemistry , physics , condensed matter physics
A stereoselective synthesis of trans ‐4‐(3‐indolylmethyl)‐3,4‐dihydrocoumarins has been developed. The method proceeds through a catalytic Friedel–Crafts reaction of coumarin‐fused donor–acceptor cyclopropanes with indoles. The use of Ni(ClO 4 ) 2 as a Lewis acid catalyst leads to the formation of a variety of 4‐(3‐indolylmethyl)‐3,4‐dihydrocoumarins in good yields with high diastereoselectivities.