Chemistry–An Asian Journal

SN1??Type Substitution Reactions of N??Protected β??Hydroxytyrosine Esters: Stereoselective Synthesis of β??Aryl and β??Alkyltyrosines

D Wilcke, E Herdtweck, T Bach

Index: Wilcke, David; Herdtweck, Eberhardt; Bach, Thorsten Chemistry - An Asian Journal, 2012 , vol. 7, # 6 p. 1372 - 1382

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Citation Number: 14

Abstract

Abstract The title compounds were prepared by aldol reaction of anisaldehyde and the respective N, N-dibenzyl glycinates. Deprotection of the nitrogen atom with Pearlman's catalyst delivered the unprotected β-hydroxytyrosine esters, which were further N-protected as N, N-phthaloyl (Phth) and N-fluorenylmethylcarbonyloxy (Fmoc) derivatives. The Friedel– Crafts reaction with various arenes was studied employing these alcohols as electrophiles ...