Allylation and propargylation of chiral cyanopropanoates: an efficient route to long chain alpha-substituted alpha-methyl alpha-amino acids

Chirality. 2004 Feb;16(2):106-11. doi: 10.1002/chir.10312.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyanates / chemistry*
  • Fatty Acids / chemical synthesis
  • Fatty Acids / chemistry
  • Lysine / analogs & derivatives*
  • Lysine / chemical synthesis*
  • Lysine / chemistry*
  • Methylation
  • Molecular Structure
  • Stereoisomerism

Substances

  • 2-methyl-2-amino-undecanoic acid
  • Cyanates
  • Fatty Acids
  • 2-methyllysine
  • Lysine