The Journal of Organic Chemistry

Prochiral recognition in the reaction of 3-substituted glutaric anhydrides with chiral secondary alcohols

PD Theisen, CH Heathcock

Index: Theisen, Peter D.; Heathcock, Clayton H. Journal of Organic Chemistry, 1993 , vol. 58, # 1 p. 142 - 146

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Citation Number: 68

Abstract

Results Anhydrides 5-9 were each allowed to react with 141'-naphthy1) ethanol (2) under the optimal conditions2 for prochiral recognition with anhydride 1 (Scheme IV). 6 The crude products were esterified by treatment with diazomethane and the diastereomeric ratios determined by integration of the methyl ester resonances in the lH NMR spectrum. The diastereomer ratios observed with anhydrides 5-9 were 16: 1, 14: 1, 7: 1, 81, and 1: 3, ...