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DOI: 10.1055/s-0029-1220013
Practical Methods for the Synthesis of Symmetrically α,α-Disubstituted α-Amino Acids
Publikationsverlauf
Publikationsdatum:
18. Mai 2010 (online)
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Abstract
This report provides an overview of the practical methods for preparing symmetrically α,α-disubstituted α-amino acids and their derivatives. Despite the growing application of this particular type of sterically constrained α-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.
1 Introduction
2 Bucherer-Bergs and Strecker Reactions of sym-Dialkyl and Cyclic Ketones
3 Dialkylation of Schiff Bases Derived from Glycine Esters
4 Dialkylation of Ethyl Isocyanoacetate
5 Dialkylation of Ethyl Nitroacetate
6 Ugi Reaction
7 Conclusions
Key words
sterically constrained - α,α-disubstituted α-amino acids - dialkylation - nucleophilic glycine equivalents - nickel(II) complexes
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