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Optically Active α‐Arylglycine Esters by Friedel‐Crafts Alkylation with the Chiral Cation of the Bislactim Ether of cyclo ‐( L ‐Val‐Gly)
Author(s) -
Schöllkopf Ulrich,
Grüttner Sabine,
Anderskewitz Ralf,
Egert Ernst,
Dyrbusch Michael
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198706831
Subject(s) - friedel–crafts reaction , racemization , alkylation , chemistry , hydrolysis , ether , epimer , optically active , adduct , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The chiral non‐racemic glycine cation equivalent 1 enabled the synthesis of the previously unknown methyl ( R )‐α‐arylglycinate 3 . The Friedel‐Crafts adducts 2 could be hydrolyzed without epimerization or racemization with 2 equivalents of 0.1 N HCl. α‐Arylglycines are of particular interest as pharmacophoric building blocks of drugs. (R 1 –R 4 H, OEt, OMe.)