Enantioselective Organocatalytic Synthesis of Arylglycines  via  Friedel–Crafts Alkylation of Arenes with a Glyoxylate Imine | Zendy

Enders Dieter | Zendy; Seppelt Matthias | Zendy; Beck Tobias | Zendy

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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.

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