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Enantioselective Organocatalytic Synthesis of Arylglycines via Friedel–Crafts Alkylation of Arenes with a Glyoxylate Imine
Author(s) -
Enders Dieter,
Seppelt Matthias,
Beck Tobias
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000143
Subject(s) - chemistry , enantiopure drug , enantioselective synthesis , imine , friedel–crafts reaction , alkylation , organic chemistry , glyoxylate cycle , enantiomer , organocatalysis , enantiomeric excess , brønsted–lowry acid–base theory , combinatorial chemistry , catalysis , enzyme
The enantioselective organocatalytic synthesis of arylglycines has been developed employing 1 mol% of an enantiopure N ‐triflyl phosphoramide Brønsted acid as organocatalyst. Various differently substituted phenylglycine derivatives can be synthesized in good to excellent yields and enantiomeric excesses based on a Friedel–Crafts alkylation of electron‐rich arenes with a glyoxylate imine. A novel protocol for the deprotection of the N ‐ tert ‐butylsulfonyl (Bus) group has also been developed.