Optically Active α‐Arylglycine Esters by Friedel‐Crafts Alkylation with the Chiral Cation of the Bislactim Ether of  cyclo ‐( L ‐Val‐Gly) | Zendy

Schöllkopf Ulrich | Zendy; Grüttner Sabine | Zendy; Anderskewitz Ralf | Zendy; Egert Ernst | Zendy; Dyrbusch Michael | Zendy

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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.)

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