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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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Supplementary files

Article information


Submitted
30 Jul 2002
Accepted
30 Sep 2002
First published
15 Oct 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 2442-2448
Article type
Paper

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, 2442
DOI: 10.1039/B207457P

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