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Issue 22, 2002
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Chiral glycine cation equivalents: N-acyliminium species derived from diketopiperazines

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Abstract

Studies towards a N,N′-bis(p-methoxybenzyl)diketopiperazine asymmetric glycine cation equivalent for the synthesis of homochiral α-amino acids are described. The oxidation of enolate 3 with molecular oxygen provides either a mixture of hydroxylated diketopiperazines 7 and 8 or trione 10 depending upon the reaction conditions. The nucleophilic reduction of trione 10 and the reaction of acetoxy N-acyliminium ion precursors 5 and 6, derived from 7 and 8, with allyltrimethylsilane and boron trifluoride etherate is examined and a model for the stereoselectivity observed in these additions is presented.

Graphical abstract: Chiral glycine cation equivalents: N-acyliminium species derived from diketopiperazines

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Publication details

The article was received on 30 Jul 2002, accepted on 30 Sep 2002 and first published on 15 Oct 2002


Article type: Paper
DOI: 10.1039/B207457P
Citation: J. Chem. Soc., Perkin Trans. 1, 2002,0, 2442-2448
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    Chiral glycine cation equivalents: N-acyliminium species derived from diketopiperazines

    S. D. Bull, S. G. Davies, A. Christopher Garner, M. D. O'Shea, E. D. Savory and E. J. Snow, J. Chem. Soc., Perkin Trans. 1, 2002, 0, 2442
    DOI: 10.1039/B207457P

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