A chiral recognition model for the chromatographic resolution of N-acylated 1-aryl-1-aminoalkanes

WH Pirkle, CJ Welch, MH Hyun

Index: Pirkle, William H.; Welch, Christopher J.; Hyun, Myung Ho Journal of Organic Chemistry, 1983 , vol. 48, p. 5022 - 5026

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Citation Number: 98

Abstract

The enantiomers of N-acyl derivatives of 1-aryl-1-aminoalkanes generally may be chromatographically separated on a silica-bonded chiral stationary phase derived from N-(3, 5-dinitrobenzoyl) phenylglycine. Chiral recognition is enhanced by increases in either the s basicity of the aryl substituent or the size of the alkyl substituent but is diminished by increases in the size of the acyl group. Carbamate and urea derivatives of these amines ...