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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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Publication details

The article was received on 02 Feb 2007, accepted on 01 Mar 2007 and first published on 09 Mar 2007


Article type: Paper
DOI: 10.1039/B701628J
Citation: New J. Chem., 2007,31, 486-495
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    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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