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Catalytic Asymmetric Friedel–Crafts Alkylation of β , γ ‐Unsaturated α ‐Ketoesters: Enantioselective Addition of Aromatic C−H Bonds to Alkenes
Author(s) -
Jensen Kim B.,
Thorhauge Jacob,
Hazell Rita G.,
Jørgensen Karl Anker
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20010105)40:1<160::aid-anie160>3.0.co;2-s
Subject(s) - friedel–crafts reaction , enantioselective synthesis , alkylation , chemistry , catalysis , aryl , organic chemistry , electrophilic aromatic substitution , alkyl
Useful catalytic BOXes : Chiral bisoxazoline (BOX)/Lewis acid complexes can catalyze highly enantioselective Friedel–Crafts alkylation reactions. The new reaction (see scheme) is successful with both aromatic and heteroaromatic compounds and with a wide range of β , γ ‐unsaturated α ‐ketoesters (R 1 = alkyl, aryl, or a protected alcohol). Products are formed with up to >99 % ee.