Stereocontrolled formation of amino acids and N-heterocycles bearing a quaternary chiral carbon.
Stereocontrolled formation of tertiary or quaternary chiral carbons bearing nitrogen was achieved using the [3,3]-sigmatropic rearrangement of cyanate to isocyanate as a key element. A short and highly selective sequence of reactions, starting from p-menthane-3-carboxaldehyde, was developed leading to alpha,alpha-dialkylated alpha-amino acids or N-heterocycles, depending on the method of cleavage of the auxiliary.
Département de Chimie, Université de Sherbrooke, Sherbrooke, QC, Canada J1K 2R1.
Stéphanie
S
Roy
Claude
C
Spino
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D001688:Biological Products; D009584:Nitrogen