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Facile entry to (−)‐( R )‐ and (+)‐( S )‐mexiletine
Author(s) -
Carocci Alessia,
Franchini Carlo,
Lentini Giovanni,
Loiodice Fulvio,
Tortorella Vincenzo
Publication year - 2000
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/(sici)1520-636x(2000)12:3<103::aid-chir1>3.0.co;2-x
Subject(s) - mexiletine , chemistry , enantiomer , enantiomeric excess , chiral stationary phase , stereochemistry , high performance liquid chromatography , chromatography , enantioselective synthesis , organic chemistry , anesthesia , catalysis , medicine
The title compounds, 1a and 1b, have been synthesized in a three‐step sequence starting from (−)‐(S) and (+)‐( R )‐propylene oxide, respectively, in acceptable overall yields. The enantiomeric excess values for 1a and 1b were 96% and 93% respectively, as assessed by HPLC analysis on a chiral stationary phase of the corresponding N ‐acetyl derivatives. The synthetic route herein presented may represent a facile entry to highly enriched mexiletine enantiomers, alternative to those previously reported in the literature. Chirality 12:103–106, 2000. © 2000 Wiley‐Liss, Inc.