Journal
SYNTHESIS-STUTTGART
Volume -, Issue 14, Pages 2319-2344Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1220013
Keywords
sterically constrained; alpha,alpha-disubstituted alpha-amino acids; dialkylation; nucleophilic glycine equivalents; nickel(II) complexes
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This report provides an overview of the practical methods for preparing symmetrically alpha,alpha-disubstituted alpha-amino acids and their derivatives. Despite the growing application of this particular type of sterically constrained alpha-amino acid in the de novo design of peptides and peptidomimetics, synthetically important achievements in the field have not been summarized so far. Classical methods, such as the Bucherer-Bergs and Strecker reactions of sym-dialkyl and cyclic ketones, as well as recent methods involving dialkylation of nucleophilic glycine equivalents and Ugi reactions, are presented.
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