Stereoselective reactions of lithium enolates derived from N-BOC protected pyroglutamic esters

Jesús Ezquerra, Concepción Pedregal, Almudena Rubio, Belén Yruretagoyena, Ana Escribano, Francisco Sánchez-Ferrando

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92 Citations (Scopus)

Abstract

The lithium enolates of N-Boc protected pyroglutamic ethyl or tert-butyl esters react with electrophiles in good yield without epimerization of the chiral centre. With benzyl bromides the process is stereospecific, yielding exclusively the trans isomer. However, with other reactive electrophiles a 2:1 trans/cis diastereomeric mixture was obtained, regardless of the steric bulk of the ester group. © 1993.
Original languageEnglish
Pages (from-to)8665-8678
JournalTetrahedron
Volume49
Issue number38
DOIs
Publication statusPublished - 17 Sep 1993

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