138313-49-2Relevant articles and documents
The synthesis of α,α-disubstituted α-amino acids via ichikawa rearrangement
Szczes?niak, Piotr,Pieczykolan, Micha?,Stecko, Sebastian
, p. 1057 - 1074 (2016/02/19)
An approach to α,α-disubstituted α-amino acids is reported. The key step is allyl cyanate-to-isocyanate rearrangement. As demonstrated, the resultant allyl isocyanates can be directly trapped with various nucleophiles, for instance, alcohols, amines, and organometallic reagents, to provide a broad range of N-functionalized allylamines. The developed method has been successfully applied in the synthesis of two bioactive peptides: 2-aminoadamantane-2-carboxylic acid derived P2X7-evoked glutamate release inhibitor and 4-amino-tetrahydropyranyl-4-carboxylic acid derived dipeptide GSK-2793660, which is currently in clinical trials as cathepsin C inhibitor for the treatment of cystic fibrosis, noncystic fibrosis bronchiectasis, ANCA-associated vasculitis and bronchiectasis.
New Syntheses of Isomerically Pure Allyl and Propargyl Cyanides by Isocyanide-Cyanide Rearrangement
Wolber, Erwin K. A.,Schmittel, Michael,Ruechardt, Christoph
, p. 525 - 532 (2007/10/02)
A new route for the synthesis of isomerically pure allyl and propargyl cyanides has been developed.Allylic amines are synthesized from the corresponding alcohols by Mitsunobu or by Overman reaction.Formylation with formic acid derivatives provides N-substituted formamides, which are dehydrated to isocyanides. 1,2-Sigmatropic rearrangement by flash pyrolysis provides the isomerically pure allyl and propargyl cyanides. Key Words: Isocyanide-cyanide rearrangment / Cyanides, allyl- and propargyl-
