REGIOSELECTIVE NUCLEOPHILIC RING OPENING REACTIONS OF 2,2-DISUBSTITUTED AZIRIDINES - THE ASYMMETRIC SYNTHESIS OF ALPHA,ALPHA-DISUBSTITUTED AMINO ACIDS

摘要

In this paper a broadly applicable synthesis of chiral alpha,alpha-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 alpha,alpha-disubstituted amino acid derivatives in good yield. Copyright (C) 1996 Elsevier Science Ltd [References: 21]