TY - JOUR
T1 - High-performance liquid chromatographic enantioseparation of methanobenzazocines
AU - Barker, William M.
AU - Worm, Karin
AU - Dolle, Roland E.
PY - 2009/11/6
Y1 - 2009/11/6
N2 - Chiral recognition and resolution of methanobenzazocines was investigated by HPLC using polysaccharide, Pirkle-type, native and derivatized β-cyclodextrin chiral stationary phases. Enantioseparation of phenyl substituted 2,6-methanobenzazocines was achieved with multiple chiral stationary phases throughout the classes described. Chiral resolution of the enantiomers of 1,5-methano-3-methyl-6-oxo-1,2,3,4,5,6-hexahydro-3-benzazocine was produced on both polysaccharide and Pirkle-type phases. In the case of 1,5-methano-3-methyl-6-phenyl-1,2,3,4,5,6-hexahydro-3-benzazocine only a dinitrophenyl substituted β-cyclodextrin produced a separation of enantiomers.
AB - Chiral recognition and resolution of methanobenzazocines was investigated by HPLC using polysaccharide, Pirkle-type, native and derivatized β-cyclodextrin chiral stationary phases. Enantioseparation of phenyl substituted 2,6-methanobenzazocines was achieved with multiple chiral stationary phases throughout the classes described. Chiral resolution of the enantiomers of 1,5-methano-3-methyl-6-oxo-1,2,3,4,5,6-hexahydro-3-benzazocine was produced on both polysaccharide and Pirkle-type phases. In the case of 1,5-methano-3-methyl-6-phenyl-1,2,3,4,5,6-hexahydro-3-benzazocine only a dinitrophenyl substituted β-cyclodextrin produced a separation of enantiomers.
KW - Benzazocine
KW - Benzomorphans
KW - Chiral separation
KW - Cyclodextrin
KW - Enantioselective
KW - HPLC
KW - Polysaccharide and Pirkle-type chiral stationary phases
KW - Racemic
UR - http://www.scopus.com/inward/record.url?scp=70349816660&partnerID=8YFLogxK
U2 - 10.1016/j.chroma.2009.08.033
DO - 10.1016/j.chroma.2009.08.033
M3 - Article
C2 - 19801151
AN - SCOPUS:70349816660
SN - 0021-9673
VL - 1216
SP - 7708
EP - 7714
JO - Journal of Chromatography A
JF - Journal of Chromatography A
IS - 45
ER -