Premium
Synthesis of (+)‐6,7‐Dimethoxy‐1,2,3,4‐tetrahydroisoquinoline‐1‐carboxylic Acid, a Diastereoselective Approach
Author(s) -
Bułyszko Ilona,
Chrzanowska Maria,
Grajewska Agnieszka,
Rozwadowska Maria D.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403218
Subject(s) - tetrahydroisoquinoline , chemistry , amine gas treating , yield (engineering) , combinatorial chemistry , stereochemistry , organic chemistry , materials science , metallurgy
The diastereoselective synthesis of (+)‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline‐1‐carboxylic acid (90 % ee ) was accomplished by employing a combination of two synthetic methods, that is, the Petasis synthesis of amino acids and the Pomeranz–Fritsch–Bobbitt synthesis of tetrahydroisoquinoline derivatives. The stereochemical outcome of the synthesis was controlled by chiral aminoacetaldehyde acetals, which were used as the amine component of the Petasis step to yield the Pomeranz–Fritsch–Bobbitt substrate for the tetrahydroisoquinoline ring formation in one simple operation.