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Efficient access to all four stereoisomers of phenylalanine cyclopropane analogues by chiral HPLC
Author(s) -
Cativiela Carlos,
DíazdeVillegas María D.,
Jiménez Ana I.,
López Pilar,
Marraud Michel,
Oliveros Laureano
Publication year - 1999
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(1999)11:7<583::aid-chir11>3.0.co;2-r
Subject(s) - chemistry , enantiomer , cyclopropane , cellulose , chiral column chromatography , amylose , high performance liquid chromatography , chirality (physics) , enantioselective synthesis , chloroform , organic chemistry , chromatography , stereochemistry , catalysis , ring (chemistry) , starch , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Bonded polysaccharide‐derived chiral stationary phases were found to be useful for the preparation of the four stereoisomers of the cyclopropane analogue of phenylalanine (c 3 Phe) as well as for the direct determination of the enantiomeric purity of c 3 Phe derivatives by HPLC. Three chiral stationary phases, consisting of cellulose and amylose derivatives chemically bonded on allylsilica gel, were tested. The mixed 10‐undecenoate/3,5‐dimethylphenylcarbamate of cellulose, 10‐undecenoate/3,5‐dimethylphenylcarbamate of amylose and 10‐undecenoate/ p ‐methylbenzoate of cellulose were the starting polysaccharide derivatives for CSP‐1, CSP‐2, and CSP‐3, respectively. Using mixtures of n ‐hexane/chloroform/2‐propanol as mobile phase on a semi‐preparative column (150 mm × 20 mm ID) containing CSP‐2, we separated about 1.7 g of racemic cis ‐methyl 1‐ tert ‐butoxycarbonylamino‐2‐phenylcyclopropanecarboxylate ( cis ‐ 6 ) and 1.2 g of racemic trans ‐methyl‐1‐ tert ‐butoxycarbonylamino‐2‐phenylcycloprop‐anecarboxylate ( trans ‐ 6 ) by successive injections. Chirality 11:583–590, 1999. © 1999 Wiley‐Liss, Inc.