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Issue 4, 2007
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On the origins of diastereoselectivity in the alkylation of diketopiperazine enolates

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Abstract

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.

Graphical abstract: On the origins of diastereoselectivity in the alkylation of diketopiperazine enolates

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Article information


Submitted
02 Feb 2007
Accepted
01 Mar 2007
First published
09 Mar 2007

New J. Chem., 2007,31, 486-495
Article type
Paper

On the origins of diastereoselectivity in the alkylation of diketopiperazine enolates

S. D. Bull, S. G. Davies, A. C. Garner, A. L. Parkes, P. M. Roberts, T. G. R. Sellers, A. D. Smith, J. A. Tamayo, J. E. Thomson and R. J. Vickers, New J. Chem., 2007, 31, 486
DOI: 10.1039/B701628J

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