Allylation and propargylation of chiral cyanopropanoates: an efficient route to long chain alpha-substituted alpha-methyl alpha-amino acids.
alpha-Methyllysine and 2-amino-2-methylundecanoic acid, two alpha,alpha-disubstituted unnatural glycines, were synthesized using highly diastereoselective allylation or propargylation of chiral (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate as the key step to introduce the long side chain. Chirality 16:106-111, 2004.
Cativiela
Carlos
C
Departamento de Química Orgánica, Facultad de Ciencias-Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza-CSIC, E-50009 Zaragoza, Spain.
Díaz-De-Villegas
María D
MD
Gálvez
José A
JA
Ronco
Eva
E
D003485:Cyanates / Q000737:chemistry*; D005227:Fatty Acids / Q000138:chemical synthesis / Q000737:chemistry; D008239:Lysine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D013237:Stereoisomerism
C406886:2-methyl-2-amino-undecanoic acid; D003485:Cyanates; D005227:Fatty Acids; C049907:2-methyllysine; D008239:Lysine