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Highly diastereoselective synthesis of enantiopure naphthylaminoalcohols with analgesic properties
Author(s) -
Azzolina Ornella,
Collina Simona,
Urbano Mariangela,
Fata Emilio,
Loddo Guya,
Linati Laura,
Lanza Enrica,
Barbieri Annalisa
Publication year - 2006
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20328
Subject(s) - enantiopure drug , chemistry , analgesic , stereochemistry , organic chemistry , combinatorial chemistry , enantioselective synthesis , catalysis , pharmacology , medicine
The diastereoselective synthesis via Grignard reaction of enantiopure analgesic naphthylaminoalcohols has been performed. The chiral racemic key intermediate 3‐dimethylamino‐2‐methyl‐1‐(naphthalen‐2‐yl)propan‐1‐one and enantiomers were prepared and transformed into the desired compounds by addition of the organometallic reagent. The chemical characterization of all diastereoisomers was accomplished by 1 H NMR and HPLC analyses and the absolute configuration assigned by CD spectroscopy. The in vitro and in vivo profile has also been evaluated. Chirality 2006. © 2006 Wiley‐Liss, Inc.
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