A stereodivergent approach to chiral nonracemic N-protected alpha,alpha-dialkylated amino acids.
Menthyl carboxaldehyde is used as a chiral auxiliary to make quaternary amino acids of either configuration via a stereodivergent approach that includes an SN2' displacement by a cuprate reagent and a Curtius rearrangement as key steps.
D000447:Aldehydes / Q000737:chemistry; D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D010421:Pentanoic Acids / Q000737:chemistry; D013237:Stereoisomerism; D014633:Valine / Q000031:analogs & derivatives / Q000138:chemical synthesis
D000447:Aldehydes; D000596:Amino Acids; D010421:Pentanoic Acids; C005566:pivalic acid; D014633:Valine