The Journal of Organic Chemistry

Synthesis and separation of diastereomeric imino alcohol derivatives of chiral phthalides: a method for assignment of phthalide absolute configurations

WH Pirkle, TJ Sowin

Index: Pirkle, William H.; Sowin, Thomas J. Journal of Organic Chemistry, 1987 , vol. 52, # 14 p. 3011 - 3017

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Citation Number: 19

Abstract

Representative members of a series of chiral type 1 phthalides were converted with Lawesson's reagent to the corresponding thionophthalides. On treatment with any of several configurationally known chiral amino alcohols in the presence of mercuric trifluoroacetate, diastereomeric imino alcohols are afforded. These prove to be readily separable by chromatography on either silica or chiral stationary phases derived from the N-3, 5- ...