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Enantioselective Friedel–Crafts Alkylation of N ‐Methylindoles with Nitroalkenes Catalyzed by Chiral Bifunctional Abietic‐Acid‐Derived Thiourea‐Zn II Complexes
Author(s) -
Huang Weigen,
Wang Hengshan,
Huang Guobao,
Wu Yongming,
Pan Yingming
Publication year - 2012
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.201200584
Subject(s) - chemistry , bifunctional , thiourea , friedel–crafts reaction , abietic acid , enantioselective synthesis , catalysis , alkylation , organic chemistry , medicinal chemistry , resin acid , rosin
The catalytic asymmetric Friedel–Crafts alkylation of N ‐methylindoles with nitroalkenes catalyzed by bifunctional abietic‐acid‐derived thiourea‐Zn II complexes was investigated. Various types of the nitroalkylated indoles were synthesized under mild conditions and obtained with excellent yields (up to 99 %) and good enantioselectivities (up to 86 % ee ). These chiral thiourea catalysts are easily available from the commercial abietic acid.