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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-butanoates and 3-methyl-aspartates in high de and ee. © 2006 Elsevier Ltd. All rights reserved.

Original publication

DOI

10.1016/j.tet.2006.05.033

Type

Journal article

Journal

Tetrahedron

Publication Date

14/08/2006

Volume

62

Pages

7911 - 7925