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



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



Tetrahedron 52(40): 13035-13050



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.

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Accession: 009318461

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