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High levels of diastereoselectivity are observed for benzylation of the lithium enolates of (S)-N,N′-bis-para-methoxybenzyl-3-iso-propyl- piperazine-2,5-dione, (S)-N(1)-para-methoxybenzyl-N(4)-methyl-3-iso-propyl- piperazine-2,5-dione and (S)-N(1)-methyl-N(4)-para-methoxybenzyl-3-iso-propyl- piperazine-2,5-dione. These data suggest that the high diastereofacial selectivity observed for alkylation of these diketopiperazine templates is mainly a consequence of the relay of stereochemical information from C(3) to C(6) via the influence of 1,2-torsional strain introduced by the N-alkyl substituents, rather than through minimisation of steric interactions alone. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Original publication

DOI

10.1039/b701628j

Type

Journal article

Journal

New Journal of Chemistry

Publication Date

16/04/2007

Volume

31

Pages

486 - 495