Tetrahedron

Enantiodiscrimination of racemic electrophiles by diketopiperazine enolates: asymmetric synthesis of methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates

SD Bull, SG Davies, SW Epstein, AC Garner, N Mujtaba…

Index: Bull, Steven D.; Davies, Stephen G.; Epstein, Simon W.; Garner, A. Christopher; Mujtaba, Nadeam; Roberts, Paul M.; Savory, Edward D.; Smith, Andrew D.; Tamayo, Juan A.; Watkin, David J. Tetrahedron, 2006 , vol. 62, # 33 p. 7911 - 7925

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Citation Number: 25

Abstract

Enolates of (S)-N, N′-bis-(p-methoxybenzyl)-3-iso-propylpiperazine-2, 5-dione exhibit high levels of enantiodiscrimination in alkylations with (RS)-1-aryl-1-bromoethanes and (RS)-2- bromoesters, affording substituted diketopiperazines containing two new stereogenic centres in high de. Deprotection and hydrolysis of the resultant substituted diketopiperazines provides a route to the asymmetric synthesis of homochiral methyl 2-amino-3-aryl- ...