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Asymmetric Organocatalytic Aza‐Friedel–Crafts Reaction of Naphthols with N ‐Sulfonyl Imines
Author(s) -
Chauhan Pankaj,
Chimni Swapandeep Singh
Publication year - 2011
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.201001653
Subject(s) - chemistry , friedel–crafts reaction , bifunctional , sulfonyl , organocatalysis , catalysis , organic chemistry , enantioselective synthesis , reaction conditions , medicinal chemistry , alkyl
The first organocatalytic asymmetric aza‐Friedel–Crafts reaction of naphthols with N ‐sulfonyl imines has been developed. The cupreine‐derived bifunctional organocatalyst BzCPN efficiently catalyzes the formation of aza‐Friedel–Crafts products in good to excellent yields (up to 99 %) with high enantioselectivities (up to 99.5:0.5 er ) under mild reaction conditions, with a low catalyst loading (2–5 mol‐%), and in an aerobic environment.