Regioselective nucleophilic ring opening reactions of 2,2-disubstituted aziridines — the asymmetric synthesis of α,α-disubstituted amino acids

In this paper a broadly applicable synthesis of chiral α,α-disubstituted amino acids is outlined based upon regioselective ring opening of aziridine derivatives. Examples of nitrogen, sulphur and carbon nucleophiles were found to preferentially attack the C3 position of chiral 2-methyl-2-silyloxymet...

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Bibliographic Details
Published in:Tetrahedron 1996-09, Vol.52 (40), p.13035-13050
Main Authors: Burgaud, Beatrice G.M., Horwell, David C., Padova, Allessandro, Pritchard, Martyn C.
Format: Article
Language:English
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Summary:In this paper a broadly applicable synthesis of chiral α,α-disubstituted amino acids is outlined based upon regioselective ring opening of aziridine derivatives. Examples of nitrogen, sulphur and carbon nucleophiles were found to preferentially attack the C3 position of chiral 2-methyl-2-silyloxymethyl aziridines to provide a range of α,α-disubstituted amino acid derivatives in good yield. The regioselective ring opening reactions of novel chiral aziridines eg. (S)-5 is described.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00784-3